Methyl 2,6-Di-O-methylsulfonyl-α-D-glucopyranoside and New Syntheses of 3,4-Di- and 3,4,6-Tri-O-methyl-D-glucose1
Methyl 2,6-Di-O-methylsulfonyl-α-D-glucopyranoside and New Syntheses of 3,4-Di- and 3,4,6-Tri-O-methyl-D-glucose1
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甲基2,6-二-O-甲磺酰基-α-D-吡喃葡萄糖苷和3,4-二-和3,4,6-三-O-甲基-D-葡萄糖的新合成1
DOI：
10.1021/jo01048a039
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发表时间：
1962
影响因子：
3.6
通讯作者：
L. Long
中科院分区：
文献类型：
--
作者：
A. Mitra;D. Ball;L. Long
通过甲基α-D-吡喃葡萄糖苷的部分甲磺酰化反应合成了甲基2，6-二-O-甲磺酰基-α-D-吡喃葡萄糖苷。描述了结晶的二-O-硝基和二-O-甲基衍生物。后者与碱水溶液皂化得到结晶的甲基3，4-二-O-甲基-α-D-葡萄糖苷，水解得到3，4-二-O-甲基-D-葡萄糖。在沸腾的甲醇中，用甲醇钠处理甲基2，6-二-O-甲磺酰基-3，4-二-O-甲基-α D-葡萄糖苷，可使6-甲磺酰氧基直接被甲醇盐取代，生成甲基3，4，6-三-O-甲基-α D-葡萄糖苷。得到结晶2-0-甲磺酰基衍生物，其特征在于水解成3，4，
Methyl 2, 6-di-O-mesyl-ar-D-glucopyranoside has been preparedby partial mesylation of methyl aD-glucopyranoside. The crystalline di-O-nitro and di-O-methyl derivatives are described. Saponification of the latter with aqueous alkali afforded crystalline methyl 3, 4-di-O-methyl-aD-glucoside, hydrolysis of which gave 3, 4-di-O-methy 1-D-glucose. Treatment of methyl 2, 6-di-0-mesyl-3, 4-di-0-methyl-aD-glucoside with sodium methoxide in boiling methanol effected direct replacement of the 6-mesyloxy group by methoxide and methyl 3, 4, 6-tri-O-methyl-aD-glucoside was formed. It gave a crystalline 2-0-mesyl derivative and was characterized by hydrolysis to 3, 4,