On the origin of the regioselectivity in glycosylation reactions of 1,2-diols

被引：14

作者：

Belen Cid, M. ^{[1
]}

Alfonso, Francisco ^{[2
]}

Alonso, Ines ^{[1
]}

Martin-Lomas, Manuel ^{[3
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ, Canto Blanco 28049, Spain

[2] CSIC Amer Vespucio, Grp Carbohidratos, Inst Invest Quim, Seville 41092, Spain

[3] Parque Tecnol San Sebastian, San Sebastian 20009, Gulpuzcoa, Spain

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 07期

关键词：

ACCEPTOR SELECTIVITY RDAS; INOSITOLPHOSPHOGLYCAN MEDIATORS; GLYCOSYLIDENE CARBENES; INOSITOL DERIVATIVES; GLYCOSIDE REACTIVITY; BUILDING-BLOCKS; BASIS-SET; DONOR; TETRASACCHARIDE; DISACCHARIDES;

D O I：

10.1039/b819452a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The assistance of neighboring protecting groups with different orientations in 1,2-diol acceptors and the reactivity of both reaction partners, the donor and the acceptor, have been evaluated as factors that determine the regioselectivity of glycosylation reactions. It has been established, by experimental and theoretical studies, that the regioselectivity for the glycosylation of a given OH group can be considerably increased by the presence of groups able to form a hydrogen bond with that OH group. Moreover higher regioselectivities are observed when armed donor/activated acceptor combinations are avoided.

引用

页码：1471 / 1481

页数：11

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