Supporting Information
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1 Supporting Information Metal-catalyzed Stereoselective and Protecting-group-free Synthesis of 1,2-cis-Glycosides Using 4,6-Dimethoxy-1,3,5-triazin-2-yl Glycosides as Glycosyl Donors Tomonari Tanaka,* 1 Naoya Kikuta, 1 Yoshiharu Kimura, 1 and Shin-ichiro Shoda 2 1 Department of Biobased Materials Science, Graduate School of Science and Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto Department of Biomolecular Engineering, Graduate School of Engineering, Tohoku University, Aoba, Sendai, Miyagi (Received March 6, 2015; CL ; t-tanaka@kit.ac.jp) Copyright The Chemical Society of Japan
2 Table of Contents Materials 2 Characterization 2 Synthesis of DMT-glycosides 2 Synthesis of alkyl glycosides 4 NMR spectra of DMT-glycosides 9 NMR spectra of alkyl glycosides 15 1
3 Materials D-Glucose (Glc), D-mannose (Man), maltose (Mal) monohydrate, and N-methylmorpholine (NMM) were purchased from Nacalai Tesque Inc. (Kyoto, Japan). Melibiose (Mel) was purchased from Wako Pure Chemical Industries (Osaka, Japan). Maltopentaose (Glc5) and 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) were purchased from Tokyo Chemical Industry Co. Ltd. (Tokyo, Japan). Tetrakis(actonitrile)copper(I) hexafluorophosphate (Cu(I)(CH3CN)4PF6), tetrakis(actonitrile)silver(i) tetrafluoroborate (Ag(I)(CH3CN)4BF4), and tetrakis(actonitrile)palladium(ii) tetrafluoroborate (Pd(II)(CH3CN)4(BF4)2) were purchased from Sigma-Aldrich Co. LLC. (MO, USA). Bis(2,4-pentanedionato)palladium(II) and bis(2,4-pentanedionato)copper(ii) were purchased from Tokyo Chemical Industry Co. Ltd. (Tokyo, Japan). Metal scavenger, SiliaMets Imidazole, was purchased from SiliCycle Inc (Québec, Canada). Anhydrous alcohols were commercially supplied. Characterization NMR spectra were recorded using a Bruker Biospin AV-600 spectrometer. ESI mass spectra were recorded using a Bruker Daltonics microtof Q-III spectrometer. Synthesis of DMT-glycosides DMT- -Glc Glc (1.08 g, 6.00 mmol) dissolved in water (30 ml) and kept at room temperature for 1 day to equilibrate the - and β-anomers. CDMT (2.11 g, 12.0 mmol) and NMM (1.65 ml, 12.0 mmol) were added to the solution and the resulting solution was stirred for 24 h at room temperature. After removing the solvent in vacuo, the residue was purified by silica gel column chromatography (CHCl3/MeOH = 7/1) and recrystallization from ethanol to give 4,6-dimethoxy-1,3,5-triazin-2-yl β-d-glucopyranoside (DMT- -Glc, 640 mg, 1.87 mmol, 31%). 1 H NMR (600 MHz, D2O); δ (ppm) 5.81 (1H, d, H-1, J1,2 = 7.8 Hz), 3.95 (6H, s, CH3), 3.83 (1H, dd, H-6), 3.67 (1H, dd, H-6), 3.59 (1H, m, H-5), 3.56 (2H, m, H-2, H-4), 3.44 (1H, m, H-3). 13 C NMR (150 MHz, D2O); δ (ppm) and (triazine), 97.1 (C-1), 76.7 (C-5), 75.4 (C-4), 72.1 (C-2), 69.1 (C-3), 60.4 (C-6), 55.9 (CH3). ESI MS; [M + Na] +, M = C11H17N3O8, calcd , found DMT- -Man Man (540 mg, 3.00 mmol) dissolved in water (15 ml) and kept at room temperature 2
4 for 1 day to equilibrate the - and β-anomers. CDMT (1.05 g, 6.00 mmol) and NMM (825 L, 6.00 mmol) were added to the solution and the resulting solution was stirred for 24 h at room temperature. After removing the solvent in vacuo, the residue was purified by silica gel column chromatography (AcOEt/MeOH = 10/1) to give 4,6-dimethoxy-1,3,5-triazin-2-yl -D-mannopyranoside (DMT- -Man, 413 mg, 1.33 mmol, 44%). 1 H NMR (600 MHz, D2O); δ (ppm) 6.25 (1H, s, H-1), 4.09 (1H, s, H-2), 3.94 (6H, s, CH3), 3.90 (1H, m, H-3), 3.76 (1H, d, H-6), (3H, m, H-4, H-5, H-6). 13 C NMR (150 MHz, D2O); δ (ppm) and (triazine), 96.7 (C-1, JC,H = Hz), 75.0 (C-5), 70.1 (C-3), 68.9 (C-2), 66.1 (C-4), 60.6 (C-6), 55.9 (CH3). ESI MS; [M + Na] +, M = C11H17N3O8, calcd , found DMT- -Mal Mal monohydrate (180 mg, 0.50 mmol) dissolved in water (2.5 ml) and kept at room temperature for 1 day to equilibrate the - and β-anomers. CDMT (176 mg, 1.00 mmol) and NMM (138 L, 1.00 mmol) were added to the solution and the resulting solution was stirred for 24 h at room temperature. After removing the solvent in vacuo, the residue was purified by two times silica gel column chromatography (AcOEt/MeOH = 5/1, CHCl3/MeOH = 5/1) to give 4,6-dimethoxy-1,3,5-triazin-2-yl -maltoside (DMT- -Mal, 101 mg, 0.20 mmol, 40%). 1 H NMR (600 MHz, D2O); δ (ppm) 5.84 (1H, d, H-1, J1,2 = 7.8 Hz), 5.37 (1H, d, H-1, J1,2 = 3.0 Hz), 3.96 (6H, s, CH3), (2H, m, H-3, H-6), 3.79 (1H, m, H-6 ), 3.74 (1H, m, H-5), (5H, m, H-4, H-6, H-3, H-5, H-6 ), 3.60 (1H, m, H-2), 3.53 (1H, dd, H-2 ), 3.36 (1H, t, H-4 ). 13 C NMR (150 MHz, D2O); δ (ppm) and (triazine), 99.6 (C-1 ), 96.9 (C-1), 76.1 (C-4), 75.9 (C-3), 75.4 (C-5), 72.9 (C-2), 72.8 (C-3 ), 72.0 (C-5 ), 71.7 (C-2 ), 69.4 (C-4 ), 60.5 and 60.4 (C-6, C-6 ), 55.9 (CH3). ESI MS; [M + Na] +, M = C17H27N3O13, calcd , found DMT- -Mel Mel (171 mg, 0.50 mmol) dissolved in water (2.5 ml) and kept at room temperature for 1 day to equilibrate the - and β-anomers. CDMT (176 mg, 1.00 mmol) and NMM (138 L, 1.00 mmol) were added to the solution and the resulting solution was stirred for 24 h at room temperature. After removing the solvent in vacuo, the residue was purified by two times silica gel column chromatography (AcOEt/MeOH = 4/1, CHCl3/MeOH = 5/1) to give 4,6-dimethoxy-1,3,5-triazin-2-yl -melibioside (DMT- -Mel, 145 mg, 0.29 mmol, 57%). 3
5 1 H NMR (600 MHz, D2O); δ (ppm) 5.80 (1H, d, H-1, J1,2 = 7.2 Hz), 4.86 (1H, d, H-1, J1,2 = 3.0 Hz), 3.97 (6H, s, CH3), 3.83 (1H, m, H-6), (4H, m, H-4, H-5, H-5, H-6), (2H, m, H-2, H-4), (2H, m, H-2, H-3), (2H, m, H-6 2), 3.50 (1H, m, H-3 ). 13 C NMR (150 MHz, D2O); δ (ppm) and (triazine), 97.9 (C-1 ), 97.0 (C-1), 75.5 (C-2), 75.3 (C-5), 72.1 (C-3), 70.7 (C-5 ), 69.5 (C-3 ), 69.2 (C-4), 69.1 (C-4 ), 68.4 (C-2 ), 65.8 (C-6), 60.6 (C-6 ), 56.0 (CH3). ESI MS; [M + Na] +, M = C17H27N3O13, calcd , found DMT- -Glc5 Glc5 (41 mg, mmol) dissolved in water (250 L) and kept at room temperature for 1 day to equilibrate the - and β-anomers. CDMT (18 mg, 0.10 mmol) and NMM (13.8 L, 0.10 mmol) were added to the solution and the resulting solution was stirred for 24 h at room temperature. After removing the solvent in vacuo, the residue was purified by silica gel column chromatography (MeCN/H2O = 5/1) to give 4,6-dimethoxy-1,3,5-triazin-2-yl -maltopentaoside (DMT- -Glc5, 24 mg, mmol, 48%). 1 H NMR (600 MHz, D2O); δ (ppm) 5.85 (1H, d, H-1, J1,2 = 8.4 Hz), 5.38 (1H, d, H-1, J1,2 = 3.6 Hz), 5.32 (3H, d, H-1, H-1, H-1, J = 3.6 Hz), 3.96 (6H, s, CH3), (4H, m, sugar-h), (15H, m, sugar-h), (9H, m, sugar-h), 3.56 (1H, d, sugar-h), 3.35 (1H, t, H-3). 13 C NMR (150 MHz, D2O); δ (ppm) and (triazine), 99.7, 99.6, and 99.4 (4C, C-1, C-1, C-1, C-1 ), 96.9 (C-1), 76.9, 76.8, 76.7, 76.1, 75.8, 75.3, 73.33, 73.30, 73.26, 72.9, 72.7, 72.0, 71.7, 71.53, 71.45, and 71.2 (sugar-c), 69.3 (C-3), 60.5, 60.4, and 60.3 (5C, C-6, C-6, C-6, C-6, C-6 ), 55.9 (CH3). ESI MS; [M + Na] +, M = C35H57N3O28, calcd , found Synthesis of alkyl glycosides All reactions were conducted using 100 mm DMT-glycoside in anhydrous alcohol solvent and 0.1 equiv. catalyst under a nitrogen atmosphere. At the completion of the reaction, SiliaMets Imidazole was added to the solution to remove the catalyst, and stirred at room temperature. After removing the metal scavenger by filtration, the filtrate was concentrated in vacuo, then the residue was analyzed by NMR spectroscopy to determine the the yield and / ratio of product. Glc- -OMe The product was purified by silica gel column chromatography (AcOEt/MeOH = 5/1) 4
6 to give methyl- -D-glucopyranoside (Glc- -OMe). 1 H NMR (600 MHz, CD3OD); δ (ppm) 4.66 (1H, d, H-1, J1,2 = 3.6 Hz), 3.81 (1H, dd, H-6), 3.67 (1H, dd, H-6), 3.61 (1H, t, H-3), 3.52 (1H, m, H-5), 3.40 (3H, s, CH3), 3.38 (1H, m, H-2), 3.28 (1H, m, H-4). 13 C NMR (150 MHz, CD3OD); δ (ppm) (C-1), 75.2 (C-3), 73.6 (C-5), 73.6 (C-2), 71.8 (C-4), 62.7 (C-6), 55.5 (CH3). ESI MS; [M + Na] +, M = C7H14O6, calcd , found Glc- -OEt The product was purified by silica gel column chromatography (AcOEt/MeOH = 5/1) to give ethyl- -D-glucopyranoside (Glc- -OEt). 1 H NMR (600 MHz, CD3OD); δ (ppm) 4.78 (1H, d, H-1, J1,2 = 3.0 Hz), (2H, dd, H-6, CH2 of Et), (2H, m, H-6, H-3), 3.57 (1H, m, H-5), 3.51 (1H, m, CH2 of Et), 3.38 (1H, dd, H-2), 3.29 (1H, t, H-4), 1.25 (3H, t, CH3). 13 C NMR (150 MHz, CD3OD); δ (ppm) 99.9 (C-1), 75.2 (C-3), (C-5), (C-2), 71.9 (C-4), 64.5 (CH2 of Et), 62.8 (C-6), 15.3 (CH3). ESI MS; [M + Na] +, M = C8H16O6, calcd , found Glc- -O i Pr The product was purified by silica gel column chromatography (AcOEt/MeOH = 5/1) to give i-propyl- -D-glucopyranoside (Glc- -O i Pr). 1 H NMR (600 MHz, CD3OD); δ (ppm) 4.88 (1H, d, H-1, J1,2 = 3.6 Hz), 3.94 (1H, m, CH of Pr), 3.78 (1H, dd, H-6), (3H, m, H-3, H-5, H-6), 3.36 (1H, dd, H-2), 3.28 (1H, t, H-4), 1.24 (3H, d, CH3), 1.18 (3H, d, CH3). 13 C NMR (150 MHz, CD3OD); δ (ppm) 98.3 (C-1), 75.1 (C-3), 73.6 (C-5), 73.5 (C-2), 72.0 (C-4), 70.9 (CH of Pr), 62.8 (C-6), 23.7 (CH3), 21.6 (CH3). ESI MS; [M + Na] +, M = C9H18O6, calcd , found Glc- -O t Bu The product was purified by silica gel column chromatography (AcOEt/MeOH = 8/1) to give tert-butyl- -D-glucopyranoside (Glc- -O t Bu). 1 H NMR (600 MHz, CD3OD); δ (ppm) 4.98 (1H, d, H-1, J1,2 = 4.2 Hz), 3.66 (1H, m, H-5), 3.63 (1H, dd, H-6), 3.59 (1H, m, H-6), 3.52 (1H, t, H-3), (2H, m, H-2, H-4), 1.18 (9H, s, CH3 3). 13 C NMR (150 MHz, CD3OD); δ (ppm) 94.6 (C-1), 76.2 (C(CH3)3), 75.2 (C-3), 73.5 (C-2), 73.1 (C-5), 72.0 (C-4), 62.7 (C-6), 28.9 (CH3). ESI MS; [M + Na] +, M = C10H20O6, calcd , found
7 Man- -OMe The product was purified by silica gel column chromatography (CHCl3/MeOH = 5/1) to give methyl- -D-mannopyranoside (Man- -OMe). 1 H NMR (600 MHz, D2O); δ (ppm) 4.50 (1H, s, H-1), 3.91 (1H, m, H-2), 3.85 (1H, m, H-6), 3.66 (1H, dd, H-6), 3.56 (1H, dd, H-3), 3.49 (1H, m, H-4), 3.46 (3H, s, CH3), 3.30 (1H, s, H-5). 13 C NMR (150 MHz, D2O); δ (ppm) (C-1, JC,H = Hz), 76.2 (C-5), 72.9 (C-3), 70.3 (C-2), 66.9 (C-4), 61.1 (C-6), 56.8 (CH3). ESI MS; [M + Na] +, M = C7H14O6, calcd , found Man- -OMe The product was purified by silica gel column chromatography (CHCl3/MeOH = 5/1) to give methyl- -D-mannopyranoside (Man- -OMe). 1 H NMR (600 MHz, CD3OD); δ (ppm) 4.65 (1H, s, H-1), 3.85 (1H, d, H-4), 3.79 (1H, s, H-2), 3.73 (1H, m, H-6), 3.67 (1H, m, H-3), 3.62 (1H, m, H-6), 3.51 (1H, m, H-5), 3.39 (3H, s, CH3). 13 C NMR (150 MHz, CD3OD); δ (ppm) (C-1, JC,H = Hz), 74.5 (C-5), 72.6 (C-3), 72.1 (C-2), 68.6 (C-4), 62.9 (C-6), 55.2 (CH3). ESI MS; [M + Na] +, M = C7H14O6, calcd , found Man-OEt The product was purified by silica gel column chromatography (CHCl3/MeOH = 5/1) to give ethyl-d-mannopyranoside (Man-OEt). The isomers were not separated. 1 H NMR (600 MHz, D2O); δ (ppm) 4.80 (s, H-1 ), 4.60 (s, H-1 ), 3.90 (H-2 ), (H-2, H-6 ), , (H-6, H-3 ), 3.56 (H-3 ), 3.49 (H-4 ), 3.30 (H-5 ), 1.14 (3H, t, CH3). 13 C NMR (150 MHz, D2O); δ (ppm) 99.5 (C-1 ), 99.4 (C-1 ) 76.2 (C-5 ), 73.0 (C-3 ), 72.1, 70.6 (C-2 ), 70.6, 70.1, 66.9 (C-4 ), 66.8, 65.6, 63.5, 61.1 (C-6 ), 60.9 (C-6 ), 14.2 and 14.0 (CH3). ESI MS; [M + Na] +, M = C8H16O6, calcd , found Man-O i Pr The product was purified by silica gel column chromatography (CHCl3/MeOH = 5/1) to give i-propyl-d-mannopyranoside (Man-O i Pr). The isomers were not separated. 1 H NMR (600 MHz, D2O); δ (ppm) 4.90 (s, H-1 ), 4.69 (H-1 ), , 3.85 (H-2 ), 3.83 (H-6 ), 3.80 (H-2 ), (H-3, H-6, H-6 ), 3.57 (H-3 ), 3.50 (t, H-4β), 3.30 (H-5 ), 1.44 (CH3), 1.11 (CH3). 13 C NMR (150 MHz, D2O); δ (ppm) 97.7 (C-1 ), 97.6 (C-1 ), 76.2 (C-5 ), 73.1, 72.7 (C-3 ), 72.0 (C-2 ), 71.1, 70.6, 70.4, 69.8, 66.9 (C-4 ), 61.1 (C-6 ), 60.9 (C-6 ), 22.3, 22.2, 20.8, and 20.1 (CH3). ESI MS; [M + Na] +, 6
8 M = C9H18O6, calcd , found Mal- -OMe The product was purified by silica gel column chromatography (AcOEt/MeOH = 1/1) to give methyl- -maltoside (Mal- -OMe). 1 H NMR (600 MHz, D2O); δ (ppm) 5.32 (1H, d, H-1, J1,2 = 3.6 Hz), 4.73 (1H, d, H-1, J1,2 = 3.6 Hz), 3.85 (1H, t, H-3), (5H, m, H-5, H-6 2, H-6 2), 3.64 (1H, m, H-5 ), 3.59 (1H, m, H-3 ), 3.55 (1H, m, H-4), (2H, m, H-2, H-2 ), 3.35 (3H, s, CH3), 3.32 (1H, H-4 ). 13 C NMR (150 MHz, D2O); δ (ppm) 99.7 (C-1 ), 99.1 (C-1), 76.9 (C-4), 73.6 (C-3), 72.9 (C-3 ), 72.7 (C-5 ), 71.8 (C-2 ), 71.1 (C-2), 70.1 (C-5), 69.4 (C-4 ), 60.6 and 60.5 (C-6, C-6 ), 55.1 (CH3). ESI MS; [M + Na] +, M = C13H24O11, calcd , found Mal- -OEt The product was purified by silica gel column chromatography (AcOEt/MeOH = 1/1) to give ethyl- -maltoside (Mal- -OEt). 1 H NMR (600 MHz, D2O); δ (ppm) 5.32 (1H, d, H-1, J1,2 = 4.2 Hz), 4.85 (1H, d, H-1, J1,2 = 3.6 Hz), 3.88 (1H, t, H-3), (3H, m, H-6 2, H-6 ), (3H, m, CH2 of Et, H-5, H-6 ), 3.65 (1H, m, H-5 ), 3.59 (1H, m, H-3 ), 3.54 (1H, m, H-4), (3H, m, CH2 of Et, H-2, H-2 ), 3.34 (1H, t, H-4 ), 1.15(3H, t, CH3). 13 C NMR (150 MHz, D2O); δ (ppm) 99.7 (C-1 ), 97.7 (C-1), 77.0 (C-4), 73.6 (C-3), 72.9 (C-3 ), 72.7 (C-5 ), 71.8 (C-2 ), 71.1 (C-2), 70.2 (C-5), 69.4 (C-4 ), 64.0 (CH2 of Et), 60.6 and 60.5 (C-6, C-6 ), 14.1 (CH3). ESI MS; [M + Na] +, M = C14H26O11, calcd , found Mel- -OMe The product was purified by silica gel column chromatography (CHCl3/MeOH = 1/1) to give methyl- -melibioside (Mel- -OMe). 1 H NMR (600 MHz, D2O); δ (ppm) 4.91 (1H, d, H-1, J1,2 = 3.6 Hz), 4.74 (1H, d, H-1, J1,2 = 3.6 Hz), (3H, m, H-4, H-5, H-6), 3.80 (1H, dd, H-3 ), 3.75 (2H, d, H-5, H-2 ), (3H, m, H-6, H-6 2), 3.59 (1H, t, H-3), 3.50 (1H, dd, H-2), 3.44 (1H, t, H-4), 3.35 (3H, s, CH3). 13 C NMR (150 MHz, D2O); δ (ppm) 99.4 (C-1 ), 99.1 (C-1), 73.3 (C-3), 71.2 (C-2), 71.0 (C-5 ), 70.1 (C-5), 69.5 (C-3 ), 69.4 (C-4), 69.2 (C-4 ), 68.4 (C-2 ), 65.6 (C-6), 61.1 (C-6 ), 55.2 (CH3). ESI MS; [M + Na] +, M = C13H24O11, calcd , found
9 Mel- -OEt The product was purified by silica gel column chromatography (CHCl3/MeOH = 1/1) to give ethyl- -melibioside (Mel- -OEt). 1 H NMR (600 MHz, D2O); δ (ppm) 4.90 (1H, d, H-1, J1,2 = 3.6 Hz), 4.86 (1H, d, H-1, J1,2 = 3.6 Hz), (3H, m, H-4, H-5, H-6), (2H, m, H-3, H-5), (2H, m, H-2, CH2 of Et), (3H, m, H-6, H-6 2), 3.62 (1H, t, H-3), (2H, m, H-2, CH2 of Et), 3.44 (1H, t, H-4), 1.16 (3H, t, CH3). 13 C NMR (150 MHz, D2O); δ (ppm) 98.1 (C-1 ), 98.0 (C-1), 73.4 (C-3), 71.2 (C-2), 71.0 (C-5 ), 70.2 (C-3 ), 69.5 (C-4, C-5), 69.2 (C-4 ), 68.4 (C-2 ), 65.6 (C-6), 64.1 (CH2 of Et), 61.1 (C-6 ), 13.3 (CH3). ESI MS; [M + Na] +, M = C14H26O11, calcd , found Glc5- -OMe The product was purified by silica gel column chromatography (MeCN/H2O = 1/1) to give methyl- -meltopentaoside (Glc5- -OMe). 1 H NMR (600 MHz, D2O); δ (ppm) 5.32 (4H, m, H-1, H-1, H-1, H-1 ), 4.74 (1H, d, H-1, J1,2 = 3.6 Hz), (4H, m, sugar-h), (14H, m, sugar-h), (2H, m, sugar-h), 3.65 (1H, m, sugar-h), (9H, m, sugar-h), 3.35 (3H, s, CH3). 13 C NMR (150 MHz, D2O); δ (ppm) 99.7, 99.6, and 99.5 (C-1, C-1, C-1, C-1 ), 99.1 (C-1), 76.9, 76.8, 76.7, 73.5, 73.33, 73.29, 72.9, 72.7, 71.7, 71.5, 71.2, 71.1, 71.0, 70.0, and 69.3 (sugar-c), 60.5 and 60.4 (C-6, C-6, C-6, C-6, C-6 ), 55.1 (CH3). ESI MS; [M + Na] +, M = C31H54O26, calcd , found
10 Figure S1. 1 H and 13 C NMR spectra of DMT- -Glc in D 2O. 9
11 Figure S2. 1 H and 13 C NMR spectra of DMT- -Man in D 2O. 10
12 Figure S3. 13 C Coupling and NOESY NMR spectra of DMT- -Man in D 2O. 11
13 Figure S4. 1 H and 13 C NMR spectra of DMT- -Mal in D 2O. 12
14 Figure S5. 1 H and 13 C NMR spectra of DMT- -Mel in D 2O. 13
15 Figure S6. 1 H and 13 C NMR spectra of DMT- -Glc 5 in D 2O. 14
16 Figure S7. 1 H and 13 C NMR spectra of Glc- -OMe in CD 3OD. 15
17 EtOH Figure S8. 1 H and 13 C NMR spectra of Glc- -OEt in CD 3OD. 16
18 Figure S9. 1 H and 13 C NMR spectra of Glc- -O i Pr in CD 3OD. 17
19 Figure S10. 1 H and 13 C NMR spectra of Glc- -O t Bu in CD 3OD. 18
20 by-product Figure S11. 1 H and 13 C NMR spectra of Man- -OMe in D 2O. 19
21 Figure S C Coupling and NOESY NMR spectra of Man- -OMe in D 2O. 20
22 Figure S13. 1 H and 13 C NMR spectra of Man- -OMe in CD 3OD. 21
23 Figure S C Coupling and NOESY NMR spectra of Man- -OMe in CD 3OD. 22
24 EtOH by-product Figure S15. 1 H and 13 C NMR spectra of Man-OEt ( mixture) in D2O. 23
25 by-product Figure S16. 1 H and 13 C NMR spectra of Man-O i Pr ( mixture) in D 2O. 24
26 Figure S17. 1 H and 13 C NMR spectra of Mal- -OMe in D 2O. 25
27 EtOH Figure S18. 1 H and 13 C NMR spectra of Mal- -OEt in D 2O. 26
28 Figure S19. 1 H and 13 C NMR spectra of Mel- -OMe in D 2O. 27
29 EtOH Figure S20. 1 H and 13 C NMR spectra of Mel- -OEt in D 2O. 28
30 Figure S21. 1 H and 13 C NMR spectra of Glc 5- -OMe in D 2O. 29
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