Concerning the reactivities of the C-1, C-2 and C-6 hydroxy groups of myo-inositol

被引：15

作者：

Anilkumar, GN ^{[1
]}

Jia, ZJ ^{[1
]}

Kraehmer, R ^{[1
]}

Fraser-Reid, B ^{[1
]}

机构：

[1] Nat Prod & Glycotechnol Res Inst Inc, Durham, NC 27707 USA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 24期

关键词：

D O I：

10.1039/a907318c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselectivities in the reactions of the three contiguous free hydroxy groups at C-6, C-1, and C-2 of 3,4,5-tri- O-benzyl-D-myo -inositol have been examined. Stannylene activation permits selective alkylation and esterification at C-1; however, acyl migration back and forth between C-1 and C-2 leads to unpredictable ratios of the isolated regioisomers. With the stable C1-alkylated products, further alkylation is regioslective for the axial C-2-OH, whereas acylation is regioselective for the equatorial C-6-OH. In most cases the 'other' regioisomer is not observed, the by-products being those of dialkylation or diacylation.

引用

页码：3591 / 3596

页数：6

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