α-D-甲基吡喃葡萄糖苷四酯的合成

Synthesis of Tetraesters of Methyl α-D-Glucopyranoside

摘要: 以α-D-甲基吡喃葡萄糖苷为原料,合成了2,3,4,6-四-O-异丁酰基-α-D-甲基吡喃葡萄糖苷(Ⅰ)、2,3,4,6-四-O-异戊酰基-α-D-甲基吡喃葡萄糖苷(Ⅱ)、2,3,4,6-四-O-3'-甲基戊酰基-α-D-甲基吡喃葡萄糖苷(Ⅲ),并根据1H NMR和HRMS进行了糖酯结构确证。结果表明:①合成产物为目标产物;②葡萄糖苷与酰氯的物质的量比为1:4.4或1:4.6,反应温度60℃,反应时间2 h,目标糖酯的合成产率最高。

Abstract: Methyl 2, 3, 4, 6-tetra-O-isobutyryl-α-D-glucopyranoside, methyl 2, 3, 4, 6-tetra-O-isovaleryl-α-Dglucopyranoside, and methyl 2, 3, 4, 6-tetra-O-(3-methylvaleryl)-α-D-glucopyranoside were synthesized from methyl α-D-glucopyranoside. The molecular structures of the tetraesters were verified by1H NMR and HRMS. The results indicated: 1) The synthetic compounds were target products. 2) The highest yield of the target glucose tetraesters was obtained when molar ratio of methyl α-D-glucopyranoside to acyl chloride was 1:4 or 1:4.6 and reacted at 60℃ for 2 hours.