甲基O-2-脱氧-6-O-苯甲酰基-3-O-苄基-2-(苄氧羰基)氨基-α-D-吡喃葡萄糖苷的合成

Synthesis of Methyl 6-O-benzoyl-3-O-benzyl-2-(benzyloxycarbonyl) amino-2-deoxy-α-D-glucopyranoside

N-乙酰胺基葡萄糖经浓硫酸催化在甲醇中回流反应得甲基O-2-脱氧-2-氨基-?-D-吡喃葡萄糖苷,与氯甲酸苄酯反应得甲基O-2-脱氧-2-(苄氧羰基)氨基-?-D-吡喃葡萄糖苷,经2,2-二甲氧基丙烷保护、苄基保护及脱二缩醛保护得甲基O-2-脱氧-3-O-苄基-2-(苄氧羰基)氨基-?-D-吡喃葡萄糖苷,最后苯甲酰基保护C6-位羟基得标题化合物(磺达肝癸钠的中间体),总收率52.3%。本路线反应条件温和、操作简便,具有较好的工艺应用前景。

A solution of N-acetyl-D-glucosamine in methanol was heated with concentrated sulfuric acid to give methyl 2-amino-2-deoxy-α-D-glucopyranoside, followed by reacting with benzyl chloroformate to afford methyl 2-（benzyloxycarbonyl）amino-2-deoxy-α-D-glucopyranoside, the latter was protected by 2,2-dimethoxypropane and benzyl-group in sequence, and then subjected to deprotection to give methyl 3-O-benzyl-2-（benzyloxycarbonyl）amino-2-deoxy-α-D-glucopyranoside, after protecting the C6-hydroxy with benzoyl-group, the title compound, served as the intermediate of fondaparinux sodium, was obtained with a total yield of 52.3%.This route is simple and easy to operate, potential for industrial production.