Supporting Information To: Synthesis of a xylo-puromycin Analogue
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1 Supporting Information To: Synthesis of a xylo-puromycin Analogue Benoît Y. Michel, Kollappillil S. Krishnakumar and Peter Strazewski* Laboratoire de Synthèse de Biomolécules, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (UMR ), Université Claude Bernard Lyon 1, 9, Villeurbanne, FRACE. Tel: (+33) strazewski@univ-lyon1.fr Table of contents Pages General methods and experimental procedures for the synthesis of,, 9 and MR spectra of: ,-di-n-butylformamidine dimethylacetal (distilled) Page 1
2 General Methods 1 H-MR spectra (300 and 00 MHz) were obtained from solutions in CDCl 3 and CD 3 D, with the residual protonated solvent signals as internal reference (7. ppm for CHCl 3, 3.31 ppm for CD HD). The chemical shifts δ H are given in ppm; the coupling constants J are given in Hertz (Hz); the signals are described as follows: ps. = pseudo, br. = broad, s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet. 13 C-MR spectra (7 and 1 MHz) were measured in CDCl 3 ; δ C (central signal) = 7 ppm and in CD 3 D δ C (central signal) = 9. ppm. The assignments of 1 H- and 13 C-MR signals were achieved with the help of D/H exchange, CSY, HSQC, HMBC and DEPT experiments. Mass spectra (MS and HRMS) were obtained using Fast Atom Bombardment (FAB from CH Cl or H /MeH 9:1) and Electro Spray Ionization (ESI, from CH Cl or DMS). Thin Layer Chromatography (TLC) was performed on pre-coated silica gel F plates with fluorescent indicator. The compounds were visualized using UV light ( nm). Free amines were visualised on TLC plates by spraying with 0% ninhydrin solutions in ethanol, followed by heating. ucleosides were visualised on TLC plates by subsequent spraying with concentrated H S followed by % naphtoresorcinol (for the ribose intermediates) or phosphomolybdic acid solutions in ethanol, followed by heating. Column chromatography was performed with flash silica gel (10-3 µm). Page
3 Experimental procedures ',-Anhydro-adenosine (). To a suspension of adenosine 3 ( g, 1.7 mmol) in dry CH 3 C (30 ml) were sequentially added H /CH 3 C (1:9; ml, mmol), then α-acetoxyisobutyryl bromide (11. ml, 7 mmol) and stirring was continued at ambient temperature. A clear solution resulted after min (and adenine as a fine colorless precipitate began to separate shortly thereafter). After 1 h, saturated ahc 3 solution (0 ml) was added cautiously and the solution was extracted with EtAc ( x 0 ml). The combined organic phase was washed (brine), dried (MgS ), filtered, and evaporated to give a colorless solid foam, which was dissolved in dry MeH (10 ml) and stirred for 1 h with 0 ml of Dowex 1 x (H ) resin (previously exchanged against Cl, washed with dry MeH and thoroughly dried under oil pump vacuum). The resin was filtered and rinsed with MeH. Evaporation of the combined filtrate and crystallization of the residue (EtH) gave microcrystalline epoxide (. g, 91%). C 10 H 11 3 (9.7). R f (DCM/MeH 9:1) = H-MR (d -DMS, 300 MHz): δ H = 3. (dd, 1 H, J = 11.7 Hz, 3 J =.0 Hz, H A '), 3. (dd, 1 H, J = 11.7 Hz, 3 J =. Hz, H B '),.19 (t, 1 H, 3 J =.1 Hz, H'),.3 (d, 1 H, 3 J =. Hz, H),.7 (d, 1 H, 3 J =. Hz, H'),.09 (br. s, 1 H, H),.3 (s, 1 H, H), 7.3 (br. s, H, H ),.19 (s, 1 H, H),.3 (s, 1 H, H). 13 C-MR (d - DMS, 300 MHz): δ C = 7. (C'),.7 (C3 ), 0.9 (C'), 1.1 (C'),.0 (C), 11.7 (C) 139. (C), 19.1 (C), 1.7 (C), 1.0 (C). LRMS (ESI + ): m/z = 0.0 (calculated for [M+H] + : 0.1). ',-Anhydro-'--(tert-butyldiphenylsilyl)-adenosine(). TBDPSCl (3.3 ml, 3.7 g, 13.mmol) was added to epoxide (3. g, 1. mmol) in anhydrous pyridine ( ml), and the solution was stirred for 1 h at ambient temperature. H (3 ml) was added, stirring was continued for 30 min, and the volatiles were evaporated. The residue was partitioned (H /CHCl 3 ), and the organic phase was washed [(H, x 100 ml); Page 3
4 ahc 3 /H ; brine] and dried (MgS ). The volatiles were evaporated to give in almost quantitative yield, which was used in the next step without chromatography. C H 9 3 Si (7.3). R f (DCM/MeH 9:1) = H-MR (CDCl 3, 300 MHz): δ H = 1.03 (s, 9 H, Si-C(CH 3 ) 3 ), 3.73 (dd, 1 H, J = 10. Hz, 3 J = 7., H A '), 3. (dd, 1 H, J = 10. Hz, 3 J =.3 Hz, H B '),.11 (d, 1 H, 3 J =.3 Hz, H),.0 (ps. t, 1 H, 3 J =.3, 7. Hz, H'),.0 (d, 1 H, 3 J =.3 Hz, H'),.01 (br. s, H, H ),.1 (s, 1 H, H), (m, H, H-m-Ar & H-p-Ar), (d, H, 3 J = 7. Hz, H-o-Ar), 7. (s, 1 H, H),.3 (s, 1 H, H). 13 C-MR (CDCl 3, 7 MHz): δ C = 19.0 (Si-C(CH 3 ) 3 ),.7 (3 C, Si-C(CH 3 ) 3 ), 7.9 (C'),.9 (C3 ), 3. (C'), 0.7 (C'), 3.9 (C), (C), 17.7 ( C, C-m-Si-Ph), 19. ( C, C-p-Si-Ph), 13., 13. ( C, C-i-Si- Ph), 13.3 ( C, C-o-Si-Ph), 13.9 (C), 19.1 (C), 1.9 (C), 1.7 (C). LRMS (ESI + ): m/z =. (calculated for [M+H] + :.). 9-['--tert-Butyldiphenylsilyl---(α--fluorenylmethoxycarbonyl-p-methoxy-L-phenylalanyl)amido--deoxy-β-D-xylofuranos-1- yl]adenine (9). The procedure to obtain 9 (7 mg, 0% from 93.9 mg of 7) is the same as for. 1 H-MR (CDCl 3, 300 MHz): δ H = 0.9 (s, 9 H, Si-C(CH 3 ) 3 ),.79 (dd, 1 H, J = 13. Hz, 3 J =. Hz, Hβ1),.9 (dd, 1 H, J = 13. Hz, 3 J = 9.0 Hz, Hβ), 3.1 (s, 3 H, CH 3 ), (m, H, H A ', H B '),.0.10 (m, 3 H, H aliph. Fl., H', CH -Fl.),.13. (m, H, Hα, CH -Fl.),.37. (m, 1 H, H'),.0 (d, 1 H, 3 J =. Hz, H),.7 (d, 1 H, 3 J =. Hz, H),. (d, H, 3 J =. Hz, H-o-Ph(Me)),.9 (d, H, 3 J =. Hz, H-m-Ph(Me)), 7.11 (ps. t, H, 3 J = 7., 7. Hz, H-m -Fl.), (m, H, H-m-Si-Ph, H-p-Si-Ph), (m, H, H-p 3 -Fl.), (m, H, H-o 1 -Fl., H-o-Si-Ph), 7.7 (d, H, 3 J = 7. Hz, H-m -Fl.),.11 (s, 1 H, H),.1 (s, 1 H, H). 13 C-MR (CD 3 D, 7 MHz): δ C =. (3 C, Si-C(CH 3 ) 3 ), 37.7 (Cβ), 7. (CH aliph. Fl.),.7 (Me), 7. (C),. (Cα),.3 (C'), 7. (CH -Fl.), 1. (C'),.0 (C'), 93. (C), 113. ( C, C-o-Ph(Me)), ( C, C-m -Fl.), 1.0 ( C, C-o 1 -Fl.), 1.7 (C), 1 ( C, C-m -Fl.), 17.3 ( C, C-p 3 -Fl.), 17.9 ( C, C-m-Si-Ph), 1.0 (C-p- Page
5 Ph(Me)), 19. ( C, C-p-Si-Ph), 130. ( C, C-m-Ph(Me)), 13., 13.9 ( C, C-o-Si-Ph), 11. (C), 13.0 (C), HRMS (ESI + ): m/z = (calculated for [M+H] + : 90.3). 9-(-Bromo-'--tert-butyldiphenylsilyl--deoxy-β-D-xylofuranos-1-yl)adenine (10). Et 3 (1 µl,.0 mg, 0.3 mmol) and Me BBr/CH Cl (0.33 M, 7. ml,. mmol) were added to a cold (-7 C) solution of the protected epoxide (0 mg, 1. mmol) in CH Cl (3 ml). Stirring was continued for 1 h, and the reaction mixture was poured into a stirred solution of aqueous saturated ahc 3 /H. The organic layer was separated, and the aqueous layer was extracted (CH Cl ). The combined organic phase was washed (brine) and dried (MgS ). Evaporation of volatiles gave a white solid (1mg, 9%) that was crystallized (THF/MeC) to give the bromo product (1 mg, 9%). C H 30 Br 3 Si (.). Mp (uncorr.): C. R f (EtAc/CyHex :1) = H-MR (d -DMS, 300 MHz): δ H = 1.00 (s, 9 H, Si-C(CH 3 ) 3 ), 3.9 (dd, 1 H, J = 11.0 Hz, 3 J =. H A '),.03 (dd, 1 H, J = 11.0 Hz, 3 J =. Hz, H B '),.3 (dd, 1 H, 3 J =.,. Hz, H'),.0 (dd, 1 H, 3 J =.1,.3 Hz, H),.9 (q ddd, 1 H, 3 J =.1,.9 Hz, H'),.9 (d, 1 H, 3 J = 3.9 Hz, H),. (d, 1 H, 3 J =.1 Hz, H), 7.33 (br. s, H, H ), (m, H, H-m-Ar & H-p-Ar), (m, H, H-o-Ar),.09 (s, 1 H, H),.1 (s, 1 H, H). 13 C-MR (d -DMS, 7 MHz): δ C = 1. (Si-C(CH 3 ) 3 ),. (3 C, Si-C(CH 3 ) 3 ), 3.1 (C),. (C'), 79.9 (C'), 0.0 (C'),. (C), 11.9 (C), 17.9, 1.0 ( C, C-m-Si-Ph), ( C, C-p-Si-Ph), 13., 13.7 ( C, C-i-Si-Ph), 13.0, 13.1 ( C, C-o-Si-Ph), 13.3 (C), 19.3 (C), 1. (C), 1.0 (C). LRMS (ESI + ): m/z = 70.1 (calculated for [M+H] + : 70.1). Page
6 H MR H' H H' ppm (t1).0 ' DMS ' ' H' A H' B H H Page H H H H H
7 ppm (t1) C C DEPT MR H ' ' ' H C C' C' C C' Page 7
8 ppm (t1) C C C C 13 C MR H ' ' C ' H C C' C' C C' DMS Page
9 CSY H ' ' ' H.0 ppm (t1 ppm (t) Page 9
10 0 100 HSQC H ' ' ' H 10 ppm (t1 ppm (t) Page 10
11 0 100 HMBC H ' ' ' H 10 ppm (t1 ppm (t) Page 11
12 1.0 t Bu H ' Page H MR TBDPS H' H' ' ' H H' A H' B H H CHCl 3 H H x H-m-Ph x H-p-Ph x H-o-Ph ppm (t1)
13 ppm (t1) C x H-m-Ph x H-p-Ph x H-o-Ph C C DEPT MR C' TBDPS ' ' C C' CHCl 3 C' ' H t Bu Page 13
14 ppm (t1) C C C x C-m-Ph x C-p-Ph x C-o-Ph x C-i-Ph C C 13 C MR TBDPS ' ' CDCl 3 ' H C C' C' C C' t Bu C- t Bu Page 1
15 CSY TBDPS ' ' ' H.0.0 ppm (t Page 1
16 0 100 HSQC TBDPS ' ' ' H 10 ppm (t1.0 ppm (t) Page 1
17 0 100 HMBC TBDPS ' ' ' H 10 ppm (t1.0 ppm (t) Page 17
18 x H-m-Ph x H-p-Ph H t Bu H' x H-o-Ph 1 H MR 3 H H TBDPS ' H ' H H H ' H DMS EtAc H' A H' B H H' EtAc Page 1 alkane ppm (t1)
19 ppm (t1) C x C-o-Ph x C-m-Ph x C-p-Ph C C C' DEPT MR C' C TBDPS ' ' 3 C' ' H DMS H t Bu Page 19
20 ppm (t1) C C C x C-o-Ph x C-m-Ph x C-i-Ph x C-p-Ph C C 13 C MR TBDPS ' ' 3 C ' H C' C' H C C' DMS t Bu C- t Bu Page 0
21 CSY TBDPS ' ' 3 ' H H pt (t1) pt (t) Page 1
22 0 100 HSQC TBDPS ' ' 3 ' H H 10 ppm (t1 ppm (t) Page
23 H MR (CH CH CH CH 3 ) Me Me (CH CH CH CH 3 ) Page 3 (CH CH CH CH 3 ) (CH CH CH CH 3 ) xme.07.0 RCH(Me) 1.00 ppm (t1)
24 C MR (CH CH CH CH 3 ) (CH CH CH CH 3 ) RCH(Me) Me Me (CH CH CH CH 3 ) (CH CH CH CH 3 ) x Me CDCl 3 ppm (t1) Page
25 Bu H H t Bu 7 1 H MR (CH CH CH CH 3 ) x H-o-Ph x H-m-Ph x H-p-Ph CH-dbf 3 TBDPS ' ' ' (CH CH CH CH 3 ) H CHCl 3 (CH CH CH CH 3 ) H (CH CH CH CH 3 ) H' A H' B H H' H' TMS H ppm (t1) Page
26 ppm (t1) x C-o-Ph x C-m-Ph x C-p-Ph CH-dbf C C 7 DEPT MR TBDPS 3 ' ' ' H Bu t Bu (CH CH CH CH 3 ) C C' C' C C' (CH CH CH CH 3 ) (CH CH CH CH 3 ) (CH CH CH CH 3 ) Page
27 t Bu 7 13 C MR (1) TBDPS ' ' 3 ' H Bu (CH CH CH CH 3 ) (CH CH CH CH 3 ) (CH CH CH CH 3 ) C- t Bu C C' (CH CH CH CH 3 ) 70 ppm (t1) Page 7
28 10 ppm (t1) CH-dbf C x C-o-Ph x C-m-Ph x C-p-Ph C C C x C-i-Ph C 7 13 C MR () TBDPS 3 ' ' H ' Bu C CDCl 3 C' C' Page
29 Bu.0 7 CSY TBDPS ' ' 3 ' H ppm (t1 ppm (t) Page 9
30 0 7 HSQC TBDPS ' ' 3 ' H Bu ppm (t1 ppm (t) Page 30
31 HMBC TBDPS ' ' 3 ' H Bu 10 ppm (t1 ppm (t) Page 31
32 t Bu Page 3 (CH Me CH CH CH 3 ) (CH CH CH CH 3 ) 1 H MR (1) 3 1 H (CHCHCHCH3) Me (CH CH CH CH 3 ) β dbf α H H ' ' ' H RC()CH Fluorenyl H-aliph. Fl. H' CH α H' H' A H β1 H β H' B H ppm (t1) alkane
33 H MR () β Me H dbf α H H H HFmoc H ' ' ' H Page 33 x H-m-Ph(Si) x H-p-Ph(Si) x H-m -Fl x H-p 3 -Fl x H-m-Ph(Me) x H-o-Ph(Me) x H-o-Ph(Si) x H-o 1 -Fl H x H-m -Fl H -H CH-dbf ppm (t1)
34 ppm (t1) C 3 1 C' C' H ' ' DEPT MR (1) H β Me α dbf H H ' Me CH Fluorenyl C CH α C' RC()CH Fluorenyl (CH CH CH CH 3 ) t Bu (CH CH CH CH 3 ) CH β (CH CH CH CH 3 ) (CH CH CH CH 3 ) alkane Page 3
35 DEPT MR () x C-o-Ph(Si) x C-p-Ph(Si) x C-m-Ph(Si) x C-p 3 -Fl H H ' ' α β H ' H dbf Me x C-m-Ph(Me) x C-m -Fl x C-o-Ph(Me) x C-m -Fl x C-o 1 -Fl CH-dbf C C 10 ppm (t1) Page 3
36 90 ppm (t1) C t Bu (CH CH CH CH 3 ) (CH CH CH CH 3 ) C- t Bu CDCl 3 C' C' C MR (1) RC()CH Fluorenyl Me H H ' ' α β H (CH CH CH CH 3 ) CH Fluorenyl ' H dbf Me (CH CH CH CH 3 ) C' CH α C CH β alkane Page 3
37 ppm (t1) H β 13 C MR () H ' ' α H H ' C-i-Ph(Me) C CH-dbf -HC()R RC()CH Fluorenyl Me dbf C C x C-o-Ph(Si) x C-m-Ph(Si) x C-m-Ph(Me) x C-p-Ph(Si) x C-p 3 -Fl C x C-o -Fl x C-m -Fl x C-o-Ph(Me) C-p-Ph(Me) x C-m -Fl x C-o 1 -Fl x C-i-Ph(Si) x C-i-Fl C Page 37
38 ppm (t) ppm (t1 CSY ' ' ' dbf H H H Me H 1 3 α β Page 3
39 ppm (t) ppm (t1 HSQC ' ' ' dbf H H H Me H 1 3 α β Page 39
40 ppm (t) ppm (t1 HMBC ' ' ' dbf H H H Me H 1 3 α β Page 0
41 t Bu alkane Page Me CD 3 H 9 1 H MR (1) EtAc CD HD H H ' ' H ' H Me H 1 3 α β H' H-aliph. Fl. H' H H' B H' A CH α H β1 H β RC()CH Fl H 0.97 ppm (t1)
42 H MR () 1 3 β x H-m-Ph(Si) x H-p-Ph(Si) Me H H α ppm (t1) H H ' ' ' H x H-o-Ph(Me) x H-m -Fl H x H-m-Ph(Me) CHCl 3 x H-p 3 -Fl x H-o-Ph(Si) x H-o 1 -Fl x H-m -Fl H H 3.3 Page
43 ppm (t1) C DEPT MR (1) Me C' C' H β Me α H H ' ' H H ' CD HD CH Fluorenyl CH α C CH β RC()CH Fluorenyl C' t Bu Page 3
44 ppm (t1) C 9 DEPT MR () H H β Me α H ' ' H H ' C x C-m-Ph(Si) x C-p 3 -Fl x C-o-Ph(Me) x C-o-Ph(Si) x C-m-Ph(Me) x C-m -Fl x C-p-Ph(Si) x C-m -Fl x C-o 1 -Fl Page
45 ppm (t1) C RC()CH Fluorenyl C' C' C' Me CH α C C MR (1) H H ' ' β Me α H H H ' CH Fluorenyl CD 3 D CH β t Bu Page
46 x C-m-Ph(Si) C MR () H β α H H ' ' ' H Me H x C-o-Ph(Si) x C-m-Ph(Me) x C-p-Ph(Si) x C-p 3 -Fl x C-m -Fl x C-m -Fl C-p-Ph(Me) x C-o-Ph(Me) C x C-o 1 -Fl C 1.0 ppm (t1) Page
47 ppm (t) ppm (t1 9 CSY ' ' ' H H H H Me H 1 3 α β Page 7
48 HSQC 100 H β α H H ' ' ' H Me H 10 ppm (t1.0 ppm (t) Page
49 H β1 H β Page Me CD HD CH 3 D H' A H MR (1) β Me H H.00 ppm (t1) α H' B CH α H' H' H CD 3H H H ' ' ' H EtAc
50 H MR () H H x H-m-Ph(Me) x H-o-Ph(Me) H H ' ' α β H ' H Me H H ppm (t1) Page 0
51 ppm (t1) C C x C-m-Ph(Me) x C-m-Ph(Me) DEPT MR H β α H H ' C' ' Me C C' ' H Me H CH α C CD HD CH β C' Page 1
52 ppm (t1) C' C C' 13 C MR (1) H β α H ' ' H H ' Me H C' CH α Me C CD3D CH β Page
53 C MR () C H H ' ' α β H C ' H Me H x C-m-Ph(Me) x C-o-Ph(Me) C-i-Ph(Me) C C C-p-Ph(Me) C 10 ppm (t1) Page 3
54 H H ' ' α β H ' H Me H CSY ppm (t1 ppm (t) Page
55 0 H H ' ' HSQC α β H ' H Me H 100 ppm (t1.0 ppm (t) Page
56 0 H H ' ' α β H ' H HMBC Me H ppm (t1.0 ppm (t) Page
57 1.001 t Bu Page H 10 1 H MR H H x H-m-Ph x H-p-Ph TBDPS Br H ' x H-o-Ph ' ' H H H H H' A DMS H' B H' H H' ppm (t1)
58 ppm (t1) C x C-o-Ph x C-m-Ph x C-p-Ph C 10 DEPT MR TBDPS Br C C' C' ' ' C' ' H H C t Bu Page
59 ppm (t1) C C C x C-m-Ph x C-o-Ph x C-p-Ph x C-i-Ph C C C MR TBDPS Br ' ' C C' C' ' H C' H C DMS t Bu C- t Bu Page 9
60 10 CSY TBDPS ' ' Br ' H H ppm (t1.0 ppm (t) Page 0
61 HSQC TBDPS ' ' Br ' H H ppm (t1.0 ppm (t) Page 1
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