NEW STRATEGY IN THE SYNTHESIS OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO), 2-DEOXY-KDO AND THIOGLYCOSIDE OF KDO

被引：56

作者：

LUBINEAU, A ^{[1
]}

AUGE, J ^{[1
]}

LUBIN, N ^{[1
]}

机构：

[1] INST CHIM MOLEC ORSAY,CNRS,CHIM ORGAN MULTIFONCTIONNELLE LAB,BAT 420,F-91405 ORSAY,FRANCE

来源：

TETRAHEDRON | 1993年 / 49卷 / 21期

关键词：

D O I：

10.1016/S0040-4020(01)81292-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

To take advantage of synthetic intermediates on the way to KDO, we developed a new strategy based on an aqueous hetero Diels-Alder reaction with a water-soluble diene derived from D-glyceraldehyde, followed by a dihydroxylation of the newly created double bond. The stereoselectivities of these reactions were investigated to give rise to 2-deoxy-KDO, which was sulfenylated via the enolate to yield beta-thioglycoside, the hydrolysis of which led to KDO.

引用

页码：4639 / 4650

页数：12

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