REGIOSPECIFIC 4,6-FUNCTIONALIZATION OF PYRANOSIDES VIA DIMETHYLBORON - BROMIDE-MEDIATED CLEAVAGE OF PHTHALIDE ORTHOESTERS

被引：15

作者：

ARASAPPAN, A ^{[1
]}

FUCHS, PL ^{[1
]}

机构：

[1] PURDUE UNIV,DEPT CHEM,W LAFAYETTE,IN 47907

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 01期

关键词：

D O I：

10.1021/ja00106a021

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient strategy for regiocontrolled differentiation of the 4,6-positions of pyranosides has been developed using dimethylboron bromide-mediated cleavage of phthalide orthoesters. The reaction proceeds under mild conditions, is tolerant of additional acetal functionality, and produces a benzoate bearing suitable functionality for intramolecular assisted cleavage in the presence of SAc, OAc, and NHAc groups.

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页码：177 / 183

页数：7

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