Divergent synthesis of various iminocyclitols from D-ribose

Σχετικά έγγραφα
Copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic acids with the assistance of isocyanide

Supporting Information

Supplementary information

Enantioselective Organocatalytic Michael Addition of Isorhodanines. to α, β-unsaturated Aldehydes

A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes

Copper-Catalyzed Oxidative Dehydrogenative N-N Bond. Formation for the Synthesis of N,N -Diarylindazol-3-ones

Synthesis and evaluation of novel aza-caged Garcinia xanthones

Vilsmeier Haack reagent-promoted formyloxylation of α-chloro-narylacetamides

Supplement: Intramolecular N to N acyl migration in conformationally mobile 1 -acyl-1- systems promoted by debenzylation conditions (HCOONH 4

Phosphorus Oxychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions

Room Temperature Highly Diastereoselective Zn-Mediated. Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled

Peptidomimetics as Protein Arginine Deiminase 4 (PAD4) Inhibitors

Synthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane and D-homoandrostane. Tandem Click reaction/cu-catalyzed D-homo rearrangement

Electronic Supplementary Information

Supporting Information

Supporting Information. Microwave-assisted construction of triazole-linked amino acid - glucoside conjugates as novel PTP1B inhibitors

Supporting Information

Metal-free Oxidative Coupling of Amines with Sodium Sulfinates: A Mild Access to Sulfonamides

9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer catalysts

Supporting Information. Experimental section

Supporting Information

Supporting information

Direct Palladium-Catalyzed Arylations of Aryl Bromides. with 2/9-Substituted Pyrimido[5,4-b]indolizines

Electronic Supplementary Information (ESI)

Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3

Supporting Information for

Supporting information

First DMAP-mediated direct conversion of Morita Baylis. Hillman alcohols into γ-ketoallylphosphonates: Synthesis of

Supporting Information

Site-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran

Supporting Information. Synthesis and biological evaluation of nojirimycin- and

Supplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%.

Fluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine Reagents. An Efficient Method for 1,3- Oxyfluorination and 1,3-Difluorination

Regioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone.

Supporting Information. Asymmetric Binary-acid Catalysis with Chiral. Phosphoric Acid and MgF 2 : Catalytic

Supporting Information. Table of Contents. II. Experimental procedures. II. Copies of 1H and 13C NMR spectra for all compounds

Supporting Information. Experimental section

and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol

Efficient and Simple Zinc mediated Synthesis of 3 Amidoindoles

Chemoselective Reduction of α-keto Amides by Nickel Catalyst

Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006

Electronic Supplementary Information

Facile construction of the functionalized 4H-chromene via tandem. benzylation and cyclization. Jinmin Fan and Zhiyong Wang*

Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst- and solvent-free thermal multicomponent domino reaction

Supporting Information

Supporting Information. Consecutive hydrazino-ugi-azide reactions: synthesis of acylhydrazines bearing 1,5- disubstituted tetrazoles

Selective mono reduction of bisphosphine

Synthesis of Imines from Amines in Aliphatic Alcohols on Pd/ZrO 2 Catalyst at Ambient Conditions

Supporting Information

Supporting Information

New Glucuronic Acid Donors for the Modular Synthesis of Heparan Sulfate Oligosaccharides

The N,S-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H. Carbonylation using Langlois Reagent as CO Source. Supporting Information.

Supplementary Data. Engineering, Nanjing University, Nanjing , P. R. China;

Tributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate

Supporting Information

Highly enantioselective cascade synthesis of spiropyrazolones. Supporting Information. NMR spectra and HPLC traces

Copper-Catalyzed Oxidative Coupling of Acids with Alkanes Involving Dehydrogenation: Facile Access to Allylic Esters and Alkylalkenes

Supporting Information One-Pot Approach to Chiral Chromenes via Enantioselective Organocatalytic Domino Oxa-Michael-Aldol Reaction

Supporting Information

Supporting Information

Supporting Information

Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006

Supporting Information To: Synthesis of a xylo-puromycin Analogue

Ligand-free Cu(II)-mediated aerobic oxidations of aldehyde. hydrazones leading to N,N -diacylhydrazines and 1,3,4-oxadiazoles

Supporting Information

Diastereoselective Access to Trans-2-Substituted Cyclopentylamines

Supporting Information

Supporting information

Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information

The Free Internet Journal for Organic Chemistry

Supporting Information. Synthesis and biological evaluation of 2,3-Bis(het)aryl-4-azaindoles Derivatives as protein kinases inhibitors

Supporting Information

Supporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process

Total Synthesis of Echinopines A and B

Hiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl

Kishore Natte, Jianbin Chen, Helfried Neumann, Matthias Beller, and Xiao-Feng Wu*

Supporting Information for. Catalytic C H α-trifluoromethylation of α,β-unsaturated Carbonyl Compounds

Supporting Information

ESI for. A simple and efficient protocol for the palladium-catalyzed. ligand-free Suzuki reaction at room temperature in aqueous DMF.

Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/ bromides in water using oxone-kx(x= Cl or Br)

Supporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of. 1,2,3-Triazole Synthesis

Supporting Information

Supporting Information

Supporting Information

Supporting Information

Natural Products Research Institute, College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Republic of Korea

SUPPORTING INFORMATION

Iodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via double C(sp 2 )-H thiolation

Aminofluorination of Fluorinated Alkenes

Supporting Information. Chemoselective Acylation of 2-Amino-8-quinolinol in the Generation of C2-Amides or C8-Esters

Aluminium-mediated Aromatic C F Bond Activation: Regioswitchable Construction of Benzene-fused Triphenylene. Frameworks

Hydrogen-bonding catalysis of sulfonium salts

Asymmetric Synthesis of New Chiral β-amino Acid Derivatives by Mannich-type Reactions of Chiral N- Sulfinyl Imidates with N-Tosyl Aldimines

Supporting Information

Supplementary!Information!

Pd Catalyzed Carbonylation for the Construction of Tertiary and

Zuxiao Zhang, Xiaojun Tang and William R. Dolbier, Jr.* Department of Chemistry, University of Florida, Gainesville, FL

Supplementary Material

Heavier chalcogenone complexes of bismuth(iii)trihalides: Potential catalysts for acylative cleavage of cyclic ethers. Supporting Information

Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes

Transcript:

Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 205 Divergent synthesis of various iminocyclitols from D-ribose Ramu Petakamsetty, Vipin Kumar Jain, Pankaj Kumar Majhi and Ramesh Ramapanicker* Department of Chemistry and Center for Environmental Science and Engineering Indian Institute of Technology Kanpur Kanpur, 20806 India rameshr@iitk.ac.in Supplementary Information Contents Page umbers. General experimental procedures and procedure for the 02 07 synthesis of benzyl derivatives for MR Correlation 2. MR correlation data for benzyl derivatives 3. and 3 C MR spectra for all the compounds 4. PLC Data 08 28 29 68 69 80

Procedure for Benzyl Protection: Compounda(0.8 g, 2 mmol, equiv) in DMF (0 ml) was added to a stirred suspension of sodium hydride (0.4 g, 6 mmol, 3 equiv) in DMF (5 ml) at 0 ºC under nitrogen atmosphere and stirring was continued for 20 min. Benzyl bromide (0.7 ml, 6 mmol, 3 equiv) was added to the reaction mixture and stirred at room temperature for 4 h. After complete disappearance of starting material on TLC, the reaction was quenched with water (30 ml). rganic layer was extracted with diethyl ether (2 20 ml), and the combined organic phases were washed with brine ( 20 ml), dried over anhydrous a 2 S 4, filtered, concentrated, and purified by column chromatography. TBDPS a, DMF, BnBr 0 C to rt 4h TBDPS 6 0 4 3 9 Ph 5 2 Ph 7 8 0a 30a (89%) Compound (30): Column chromatography (petroleum ether/etac, 9:); oily liquid (0.2 g, 0.33 mmol, 89%); [α] 25 D = +2.8 (c 0.8, CCl 3 ); IR ν max (thin film):3068, 56 cm - ; MR (500 Mz, CDCl 3 ): δ 7.74-7.68 (m, 4, Ar-), 7.45-7.7 (m, 6, Ar-), 4.73-4.7 (m,, C 3 ), 4.66 (m, 3, C,C 0 ), 4.56 (d, J = 6.3 z,, C 2 ), 4. (d, J = 3.7 z,, C 0 ), 4.07-4.04 (m,, C 5 ), 3.97-3.92 (m, 2, C 6 ), 3.55-3.52 (m,, C 5 ), 3.43-3.39 (m,, C 4 ), 3.9-3.6 (m,, C ),.50 (s, 3, C 7 ),.3 (s, 3, C 8 ),.08 (s, 9, (C 3 ) 3 C-Si) ppm; 3 C MR (25 Mz, CDCl 3 ): δ 4.0(C-Ar), 35.8(C-Ar), 35.7(C-Ar), 33.7(C-Ar), 29.7(C-Ar), 28.6(C-Ar), 28.5(C-Ar), 28.4(C-Ar), 27.7(C-Ar), 27.0(C- Ar), 5.5(C-9), 82.(C-), 8.(C-0), 66.6(C-3), 66.5(C-2), 65.3(C-5), 62.6(C-6), 59.3(C-), 52.5(C- 4), 27.0 ((C 3 ) 3 C-Si), 26.5(C-8), 24.8(C-7), 9.3(C-Si) ppm RMS (ESI-TF) m/z [M+] + calcd for C 39 48 4 Si 622.3353; found 622.3354. 2

MM 8a a, DMF, BnBr 0 C to rt 4h Ph Ph 9 0 5 6 MM 2 3 4 8 7 3a (85%) Compound(3a): In a similar manner as described for compound 30a, Column chromatography (petroleum ether/etac, 9:); oily liquid (0.7 g, 0.39mmol, 85%);[α] 25 D = -9.3 (c 0.2, CCl 3 ); IR ν max (thin film): 3028, 495 cm - ; MR (500 Mz, CDCl 3 ): δ 7.32-7.23 (m, 0, Ar-), 4.64 (d,j = 6.7 z,, --C 2 --), 4.6 (d,j= 7.3z,, --C 2 --), 4.56 (d, J =.6 z,, C 0 ), 4.48-4.44 (m, 2, C 6, C 0 ), 4.6-4. (m, 2, C 6, C 9 ), 3.88-3.84 (m,, C 2 ), 3.8 (dd,j = 0.7, 2. z,, C 3 ), 3.59 (dd,j =.0, 4.2 z,, C 4 ), 3.30 (s, 3, -C 3 ), 3.26 (d,j = 3.6z,, C 9 ), 2.77 (dd,j =.0, 5.5 z,, C ), 2.5-2.48 (m,, C 5 ), 2.36-2.33 (t, J =.0 z,, C ),.54 (s, 3, C 7 ),.39 (s, 3, C 8 ) ppm; 3 C MR (25 Mz, CDCl 3 ): δ 39.0(C-Ar), 38.(C-Ar), 28.9(C-Ar), 28.4(C- Ar), 28.3(C-Ar), 27.9(C-Ar), 27.7(C-Ar), 27.0(C-Ar), 09.4(C-), 95.9(--C 2 --), 74.9(C-0), 74.5(C-9), 73.4(C-2), 7.7(C-3), 68.7(C-4), 63.6(C-6), 57.(-C 3 ), 55.5(C-5), 50.5(C-), 28.2(C-8), 26.3(C-7) ppm; RMS (ESI-TF) m/z [M+] + calcd for C 25 34 5 428.2437; found 428.243. Ph MM. a, DMF, BnBr 0 C to rt 4h 2. 2, Pd/C,rt, 4 h Me MM 0 5 6 2 4 3 8 9 8b 3b (69%) 7 3

Compound(3b):Column chromatography (petroleum ether/etac, :); oily liquid (0. g, 0.32mmol, 69%);[α] 25 D = +2.2 (c 0.8, CCl 3 ); IRν max (thin film): 308, 495 cm - ; MR (500 Mz, CDCl 3 ): δ 7.30-7.32 (m, 4, Ar-), 7.28-7.26 (m,, Ar-), 4.74 (d, J = 6.8 z,, --C 2 --), 4.66 (d, J = 6.8 z,, --C 2 --), 4.57 (d, J = 2.0 z,, C 9 ), 4.5 (d, J = 2.0 z,, C 9 ), 4.35 (dd,j = 6.8, 4.0 z,, C 3 ), 4.24 (dd, J = 7.4, 2.8 z,, C 4 ), 3.82-3.80 (m,, C 2 ), 3.55-3.49 (m, 2, C 6 ), 3.37 (s, 3 C 3 ), 3.09 (dd, J = 3., 6.8 z,, C ), 3.03 (dt, J = 6.8, 2.3 z,, C 5 ), 2.88 (dd, J = 3., 4.6 z,, C ), 2. (bs,, 0 ).42 (s, 3, C 7 ),.38 (s, 3, C 8 )ppm; 3 C MR (25 Mz, CDCl 3 ): δ 38.2(C-Ar), 28.4(C-Ar), 27.8(C-Ar), 27.7(C-Ar), 09.4(C-), 96.(--C 2 --), 73.8(C-9), 73.4(C-2), 73.0(C-3), 70.0(C-4), 69.8(C-6), 55.6(-C 3 ), 54.(C-5), 44.9(C-), 26.0(C-8), 25.0(C-7) ppm; RMS (ESI-TF) m/z [M+] + calcd for C 8 28 5 338.967; found 338.969. TBDPS 23a a, DMF, BnBr 0 C to rt 4h Ph TBDPS 9 Ph 8 7 6 0 2 3 2 32a (85%) 5 4 Compound(32a):Column chromatography (petroleum ether/etac, 9:); oily liquid (0.5 g, 0.23mmol 85%); [α] 25 D = -30.64 (c 0.2, CCl 3 ); IR ν max (thin film): 3060, 536 cm - ; MR (500 Mz, CDCl 3 ): δ 7.68-7.64 (m, 4, Ar-), 7.42-7.4 (m, 6, Ar-), 4.46-4.35 (m, 3, C 8, C 3 ), 4.3 (d, J = 2.8 z, 2, C 2 ), 4.02-3.97 (m, 2, C 9 ), 3.90 (dd, J = 5.5, 9.5 z,, C 5 ), 3.79 (d, J = 4.9 z,, C 9 ), 3.29-3.23 (m, 3C, C 6 ),.97-.9 (m,, C 4 ),.8-.75 (m,, C 4 ),.55 (s, 3, C 0 ),.35 (s, 3, C ),.05 (s, 9, (C 3 ) 3 C-Si) ppm; 3 C MR (25 Mz, CDCl 3 ): δ 4.9(C-Ar), 38.6(C-Ar), 35.7(C-Ar), 35.6(C-Ar), 34.9(C-Ar), 33.7(C-Ar), 29.7(C-Ar), 29.6(C-Ar), 28.7(C-Ar), 28.6(C- Ar), 28.5(C-Ar), 28.4(C-Ar), 28.2(C-Ar), 28.0(C-Ar), 27.7(C-Ar), 27.6(C-Ar), 27.5(C-Ar), 26.5(C-Ar), 08.0(C-2), 73.0(C-8), 73.00(C-6), 72.8(C-9), 7.6(C-7), 63.3(C-2), 58.0(C-3), 55.9(C-), 4

55.2(C-5), 27.5(C-4), 27.5(C-0), 26.9(C 3 ) 3 C-Si, 24.8(C-), 9.3(C-Si) ppm; RMS (ESI-TF) m/z [M+] + calcd for C 40 50 4 Si 636.3509; found 636.3509. TBDPS 23b a, DMF, BnBr 0 C to rt 4h Ph TBDPS 9 Ph 8 7 6 0 2 3 2 5 4 32b (89%) Compound(32b):Column chromatography (petroleum ether/etac, 9:); oily liquid (0.2 g, 0.3mmol 89%); [α] 25 D = -9. (c 0.8, CCl 3 ); IR ν max (thin film):3059, 589 cm - ; MR (400 Mz, CDCl 3 ): δ 7.62-7.54 (m, 4Ar-), 7.40-7.2 (m, 6, Ar-), 4.38-4.35 (m,, C 2 ), 4.33-4.34 (m, 2, C 8, C 3 ), 4.28-4.20 (m,, C 8 ), 3.90-3.84 (m, 2, C 6 ), 3.77-3.7 (m, 2, C 9 ), 3.44-3.40 (m,, C 7 ), 3.32-3.28 (m,, C 7 ), 3.7-3.2 (m,, C ) 2.94-2.88 (m,, C 5 ),.92-.86 (m,, C 4 ),.76-.68 (m,, C 4 ),.50 (s, 3, C ),.33 (s, 3, C 0 ), 0.99 (s, 9, (C 3 ) 3 C-Si)) ppm; 3 C MR (00 Mz, CDCl 3 ): δ 4.9(C-Ar), 38.3(C-Ar), 35.69(C-Ar), 35.6(C-Ar), 33.7(C-Ar), 33.6(C-Ar), 29.5(C-Ar), 28.3(C-Ar), 28.0(C-Ar), 27.8(C-Ar), 27.6(C-Ar), 27.5(C-Ar), 26.3(C-Ar), 08.2(C- 2), 73.2(C-8), 73.(C-3), 72.9(C-2), 72.4(C-6), 64.0(C-7), 62.6(C-9), 58.6(C-), 53.0(C-5), 28.4(C-4), 28.(C-0), 26.8(C 3 ) 3 C-Si, 25.6(C-), 9.2(C-Si) ppm RMS (ESI-TF) m/z[(m+)-(cl)] + calcd for C 40 50 4 Si 636.3509; found 636.3509. Ph MM a, DMF, BnBr 0 C to rt 4h Ph 8 9 6 7 5 MM 3 2 4 2 29a 0 33a (86%) 5

Compound(33a):Column chromatography (petether/ethyl acetate 8:2); oily liquid (0.3 g, 0.67 mmol 86%); [α] 25 D = +8.6 (c 0.22, CCl 3 ); IR ν max (thin film): 2947, 436 cm - ; MR (500 Mz, CDCl 3 ): δ 7.38-7.2 (m, 0, Ar-), 4.56-4.4 (m, 4, --C 2 --, C 4, C 9 ), 4.49-4.46 (m, 2, C 9, C 3 ), 4.00 (d, J = 9.7 z,, C 5 ), 3.78 (d, J = 4.3 z,, C 8 ), 3.60 (d, J = 4.3 z,, C 8 ), 3.56 (dd, J = 9.7, 7. z,, C 7 ), 3.47 (dd, J = 9.7, 5.7 z,, C 7 ), 3.44-3.40 (m,, C ), 3.29 (s, 3, -C 3 ), 3.20 (dd, J = 4.3, 0.0 z,, C 6 ), 2.65 (d, J = 4.9 z,, C 6 ),.90-.83 (m, 2, C 2 ),.54 (s, 3, C ),.38 (s, 3, C 0 ) ppm; 3 C MR (25 Mz, CDCl 3 ): δ 40.0 (C-Ar), 38.3 (C-Ar), 28.8 (C-Ar), 28.4 (C-Ar), 28.3 (C-Ar), 27.9 (C-Ar), 27.6 (C-Ar), 27.0 (C-Ar), 07.7 (C-2), 94.9 (-- C 2 --), 79.2 (C-9), 73.4 (C-4), 73. (C-3), 72.7 (C-5), 69.8 (C-8), 56.0 (C-7), 55.6 (-C 3 ), 50.6 (C-), 50. (C-6), 36.2 (C-2), 29.7 (C-0), 25.9 (C-) ppm; RMS (ESI-TF) m/z [M+] + calcd for C 26 36 5 442.2593; found 442.259. Ph MM a, DMF, BnBr 0 C to rt 4h Ph 8 9 6 7 5 MM 3 2 4 2 29b 0 33b (86%) Compound(33b):Column chromatography (petether/ethyl acetate 8:2); oily liquid (0.25 g, 0.56 mmol, 87%); [α] 25 D = +3.3 (c.6, CCl 3 ); IR ν max (thin film): 2947, 436 cm - ; MR (400 Mz, CDCl 3 ): δ 7.36-7.22 (m, 0, Ar-), 4.62 (d, J = 8.6 z,, --C 2 --), 4.55-4.39 (m, 5, --C 2 --, C 4, C 9, C 3 ), 3.93-3.90 (m, 2, C 5, C 8 ), 3.79 (dd, J = 2.6, 8.6 z,, C 7 ), 3.74 (d, J = 7.7 z,, C 8 ), 3.47 (dd, J = 2.0, 6.3 z,, C 7 ), 3.28 (s, 3, -C 3 ), 3.9-3.4 (m, 2, C 6, C ), 2.70 (dd, J = 8.9, 6.9 z,, C 6 ), 2.37-2.28 (m,, C 2 ), 2.0-2.06 (m,, C 2 ),.47 (s, 3, C ),.36 (s, 3, C 0 ) ppm; 3 C MR (00 Mz, CDCl 3 ): δ 40.3 (C-Ar), 38.5 (C-Ar), 28.5 (C-Ar), 28.4 (C-Ar), 28.3 (C-Ar), 27.6 (C-Ar), 27.0 (C-Ar), 07.4 (C-2), 96.3 (--C 2 --), 78.3 (C-9), 75.5 (C-4), 73.9 6

(C-3), 73.3 (C-5), 70.4 (C-8), 59.4 (C-7), 58.2 (-C 3 ), 55.4 (C-), 48.3 (C-6), 32.4 (C-2), 26.8 (C-0), 24.3 (C-) ppm; RMS (ESI-TF) m/z [M+] + calcd for C 26 36 5 442.2593; found 442.2596. 7

MR Correlation data for benzyl derivatives Compound 30 TBDPS Bn Bn MR (500 Mz, CDCl 3 ) TBDPS Bn Bn 3 C MR (25 Mz, CDCl 3 ) 8

TBDPS Bn Bn - CSY (500 Mz) 9

TBDPS 5 4 Bn 2 3 Bn ne spectrum (irradiation of -4) 0

Compound 3a Bn Bn MM MR (500 Mz, CDCl 3 ) Bn Bn MM 3 C MR (25 Mz, CDCl 3 )

Bn Bn MM - CSY (500 Mz) 2

5.4% 5 MM 4 Bn 6 2 Bn 3 ne spectrum (irradiation of -2) 3

Compound 3b Bn MM MR (500 Mz, CDCl 3 ) spectrum of Bn MM 3 C MR (25 Mz, CDCl 3 ) 4

Bn MM - CSY (500 Mz) 5

5 MM 4 Bn Bn 2 3.2% ne spectrum (irradiation of -4) 6

Compound32a TBDPS Bn Bn MR (500 Mz, CDCl 3 ) TBDPS Bn Bn 3 C MR (25 Mz, CDCl 3 ) 7

TBDPS Bn Bn -.- - - CSY (500 Mz) 8

TBDPS 5 6 Bn Bn 2 4 ne spectrum (irradiation of -2) 9

Compound 32b TBDPS Bn Bn MR (500 Mz, CDCl 3 ) TBDPS Bn Bn 3 C MR (25 Mz, CDCl 3 ) 20

TBDPS Bn Bn - CSY (500 Mz) 2

7.9% TBDPS 5 6 Bn Bn 2 4 3.2% ne spectrum (irradiation of -2) 22

Compound 33a Bn Bn MM MR (500 Mz, CDCl 3 ) Bn Bn MM 3 C MR (25 Mz, CDCl 3 ) 23

Bn Bn MM - CSY (500 Mz) 24

4.8% 3 2 Bn 7 MM 4 5 Bn ne spectrum (irradiation of -2) 25

Compound 33b Bn Bn MM MR (500 Mz, CDCl 3 ) Bn Bn MM 3 C MR (25 Mz, CDCl 3 ) 26

Bn Bn MM - CSY (500 Mz) 27

8.8% 8.2% 3 2 Bn 7 MM 4 5 Bn ne spectrum (irradiation of -2) 28

Compound 6 TBDPS MR (500 Mz, CDCl 3 ) TBDPS 3 C MR (25 Mz, CDCl 3 ) 29

Compound 7 TBDPS Ms MR (500 Mz, CDCl 3 ) TBDPS Ms 3 C MR (25 Mz, CDCl 3 ) 30

Compound 8 TBDPS Ms MR (500 Mz, CDCl 3 ) TBDPS Ms 3 C MR (25 Mz, CDCl 3 ) 3

Compound 9 MR (500 Mz, CDCl 3 ) TBDPS Ms 3 C MR (25 Mz, CDCl 3 ) 32

Compound0a TBDPS Ms Cbz Cbz MR (500 Mz, CDCl 3 ) TBDPS Ms Cbz Cbz 3 C MR (25 Mz, CDCl 3 ) 33

Compound0b TBDPS Ms Cbz Cbz MR (500 Mz, CDCl 3 ) TBDPS Ms Cbz Cbz 3 C MR (25 Mz, CDCl 3 ) 34

Compound a TBDPS 6 4 3 2 9 7 8 5 MR (500 Mz, CDCl 3 ) TBDPS 6 4 3 2 9 7 8 5 3 C MR (25 Mz, CDCl 3 ) 35

Compound b TBDPS 6 4 3 2 9 7 8 5 MR (500 Mz, CDCl 3 ) TBDPS 6 4 3 2 9 7 8 5 3 C MR (25 Mz, CDCl 3 ) 36

Compounda 7 5 Cl 2 4 3 6 MR (500 Mz, D 2 ) spectrum of 7 5 Cl 2 4 3 6 3 C MR (25 Mz, D 2 ) spectrum of compound a 37

Compoundb 4 2 3 Cl 2 3 4 MR (400 Mz, D 2 ) 4 2 3 Cl 2 3 4 3 C MR (00 Mz, D 2 ) 38

Compound2 TBDPS MM MR (500 Mz, CDCl 3 ) TBDPS MM 3 C MR (25 Mz, CDCl 3 ) 39

Compound 3 MM MR (500 Mz, CDCl 3 ) MM 3 C MR (25 Mz, CDCl 3 40

Compound 4 Ms MM MR (500 Mz, CDCl 3 ) Ms MM 3 C MR (25 Mz, CDCl 3 ) 4

Compound 5 MM Ms MR (500 Mz, CDCl 3 ) MM Ms 3 C MR (25 Mz, CDCl 3 ) 42

Compound6 MM Ms MR (500 Mz, CDCl 3 ) MM Ms 3 C MR (25 Mz, CDCl 3 ) 43

Compound7a Ms Cbz Cbz MM MR (500 Mz, CDCl 3 ) Ms Cbz Cbz MM 3 C MR (25 Mz, CDCl 3 ) 44

Compound7b Cbz Cbz Ms MM MR (500 Mz, CDCl 3 ) Cbz Cbz Ms MM 3 C MR (25 Mz, CDCl 3 ) 45

Compound8a MM 2 3 5 4 9 7 6 8 MR (500 Mz, CDCl 3 ) MM 2 5 3 4 9 7 6 8 3 C MR (25 Mz, CDCl 3 ) 46

Compound8b MM 2 3 5 4 9 7 6 8 MR (500 Mz, CDCl 3 ) MM 2 5 3 4 9 7 6 8 3 C MR (25 Mz, CDCl 3 ) 47

Compound2a 6 Cl 2 5 3 4 7 MR (500 Mz, D 2 ) 6 Cl 2 5 3 4 7 3 C MR (25 Mz, D 2 ) 48

Compound 2b 6 Cl 2 5 3 4 7 MR (500 Mz, D 2 ) 6 Cl 2 5 3 4 7 3 C MR (00 Mz, D 2 ) 49

Compound 9 TBDPS Et MR (500 Mz, CDCl 3 ) TBDPS Et 3 C MR (25 Mz, CDCl 3 ) 50

Compound 20 TBDPS Ms C 2 Et MR (500 Mz, CDCl 3 ) TBDPS Ms C 2 Et 3 C MR (25 Mz, CDCl 3 ) 5

Compound2 TBDPS Ms C MR (500 Mz, CDCl 3 ) TBDPS Ms C 3 C MR (25 Mz, CDCl 3 ) 52

Compound2a TBDPS Ms Cbz Cbz MR (500 Mz, CDCl 3 ) TBDPS Ms Cbz Cbz 3 C MR (25 Mz, CDCl 3 ) spectrum of compound 22a 53

Compound 22b TBDPS Ms Cbz Cbz MR (500 Mz, CDCl 3 ) TBDPS Ms Cbz Cbz 3 C MR (25 Mz, CDCl 3 ) 54

Compound 23a TBDPS 7 6 2 3 2 0 5 4 MR (500 Mz, CDCl 3 ) TBDPS 7 6 2 3 2 0 5 4 3 C MR (25 Mz, CDCl 3 ) 55

Compound 23b TBDPS 7 6 2 3 2 0 5 4 MR (500 Mz, CDCl 3 ) TBDPS 7 6 2 3 2 0 5 4 3 C MR (25 Mz, CDCl 3 ) 56

Compound 3a 8 2 3 Cl 6 7 4 5 MR (500 Mz, CD 3 D) 8 2 3 Cl 6 7 4 5 3 C MR (25 Mz, CD 3 D) 57

Compound 3b 8 2 3 Cl 6 7 4 5 MR (500 Mz, D 2 ) spectrum of 8 2 3 Cl 6 7 4 5 3 C MR (25 Mz, D 2 ) 58

Compound24 TBDPS MM Et MR (500 Mz, CDCl 3 ) TBDPS MM Et 3 C MR (25 Mz, CDCl 3 ) 59

Compound25 MM Et MR (500 Mz, CDCl 3 ) MM Et 3 C MR (25 Mz, CDCl 3 ) 60

Compound26 Ms MM Et MR (500 Mz, CDCl 3 ) Ms MM Et 3 C MR (25 Mz, CDCl 3 ) 6

Compound27 Ms MM MR (500 Mz, CDCl 3 ) Ms MM 3 C MR (25 Mz, CDCl 3 ) 62

Compound28a Ms MM Cbz Cbz MR (500 Mz, CDCl 3 ) Ms MM Cbz Cbz 3 C MR (25 Mz, CDCl 3 ) 63

Compound28b Ms MM Cbz Cbz MR (500 Mz, CDCl 3 ) Ms MM Cbz Cbz 3 C MR (25 Mz, CDCl 3 ) 64

Compound29a 6 7 5 MM 3 2 4 2 0 MR (500 Mz, CDCl 3 ) 6 7 5 MM 3 2 4 2 0 3 C MR (25 Mz, CDCl 3 ) 65

Compound29b 6 7 5 MM 3 2 4 2 0 MR (500 Mz, CDCl 3 ) 6 7 5 MM 3 2 4 2 0 3 C MR (25 Mz, CDCl 3 ) 66

Compound4a 7 2 8 6 3 4 5 MR (400 Mz, D 2 ) spectrum of 7 2 8 6 3 4 5 3 C MR (00 Mz, D 2 ) spectrum of compound4a 67

Compound4b 7 2 8 6 3 4 5 MR (400 Mz, D 2 ) 7 2 8 6 3 4 5 3 C MR (00 Mz, D 2 ) 68

PLC DATA PLC data of compound 0 (racemic) 69

PLC data of compound 0a 70

PLC data of compound 0b 7

PLC data of compound 7 (racemic) 72

PLC data of compound 7a 73

PLC data of compound 7b 74

PLC data of compound 22 (racemic) 75

PLC data of compound 22a 76

PLC data of compound 22b 77

PLC data of compound 28 (racemic) 78

PLC data of compound 28a 79

PLC data of compound 28b 80

2025 © DocPlayer.gr Πολιτική Απορρήτου | Όροι Χρήσης | Σχόλια