One-pot conversion of glycals to cis-1,2-isopropylidene-alpha-glycosides.
One-pot conversion of glycals to cis-1,2-isopropylidene-alpha-glycosides.
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将糖醛一锅转化为顺式-1,2-异丙叉-α-糖苷。
DOI：
10.1021/jo034386i
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发表时间：
2003
期刊：
影响因子：
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通讯作者：
Seeberger,PeterH
中科院分区：
文献类型：
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作者：
Lohman,GregoryJS;Seeberger,PeterH
描述了将糖醛转化为相应的1,2-顺式异丙叉-α-糖苷的一般方法。用二甲基二环氧乙烷对糖醛进行环氧化，然后在 ZnCl2 催化下添加丙酮，将多种受保护的糖醛转化为 1,2-顺式异丙叉-α-糖苷，收率良好。该反应与一系列保护基团兼容，包括酯、苄基醚和甲硅烷基醚，以及游离羟基。该方法已用于开发受保护的葡萄糖醛酸1的合成，这是糖胺聚糖合成中的关键中间体。化合物 1 经七步生产，总产率为 32%。
Described is a general method for the conversion of glycals to the corresponding 1,2-cis-isopropylidene-α-glycosides. Epoxidation of glycals with dimethyldioxirane followed by ZnCl2-catalyzed addition of acetone converted a variety of protected glycals into 1,2-cis-isopropylidene-α-glycosides in good yield. The reaction is compatible with a range of protecting groups, including esters, benzyl ethers, and silyl ethers, as well as free hydroxyl groups. This method has been applied to develop a synthesis of protected glucuronic acid1, a key intermediate in the synthesis of glycosaminoglycans. Compound1was produced in seven steps and 32% overall yield.