BENZYL ALPHA-D-MANNOPYRANOSIDE synthesis
- Product Name:BENZYL ALPHA-D-MANNOPYRANOSIDE
- CAS Number:15548-45-5
- Molecular formula:C13H18O6
- Molecular Weight:270.28
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Yield:15548-45-5 81%
Reaction Conditions:
with acetyl chloride at 50; for 2 h;
Steps:
4.2.1 Benzyl α-D-mannopyranoside (10)
A solution of D-mannose 9 (10.0g, 55.5mmol) in 80mL benzyl alcohol containing 4mL acetyl chloride was heated at 50°C for 2h and then cooled to room temperature. Benzyl alcohol was removed under high vacuum pump at 75°C. The residue was then titrated with ethyl acetate to form precipitate. The precipitate was collected by filtration and washed with ethyl acetate to give a white solid 10 (12.1g, 81%). 1H NMR (CD3OD, 400MHz): δ 3.61-3.66 (m, 2H), 3.71-3.75 (m, 2H), 3.84-3.87 (m, 2H), 4.52 (d, J=11.6Hz, 1H), 4.75 (d, J=11.6Hz, 1H), 4.84 (s, 1H); 13C NMR (CD3OD, 100MHz): δ 62.93, 68.63, 69.87, 72.19, 72.63, 74.86, 100.65, 128.76, 129.11, 129.38, 139.00. HRMS: m/z calcd for C13H19O6 [M+H]+ 271.1176, found 271.1173.
References:
Li, Tiehai;Wen, Liuqing;Williams, Adriel;Wu, Baolin;Li, Lei;Qu, Jingyao;Meisner, Jeffrey;Xiao, Zhongying;Fang, Junqiang;Wang, Peng George [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 3,p. 1139 - 1147]
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