Mirror-image carbohydrates: Synthesis of the unnatural enantiomer of a blood group trisaccharide

被引：33

作者：

Boulineau, FP ^{[1
]}

Wei, A ^{[1
]}

机构：

[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 10期

关键词：

D O I：

10.1021/jo035789l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methyl D-glucoside and D-glucose pentaacetate are transformed, respectively, into methyl alpha-O-glucuronide 3 and hydroxymethyl beta-C-glucuronide 9, which undergo decarboxylative elimination efficiently to produce 4-deoxypentenoside 4 and L-glucal 10. These unsaturated pyranosides provide an expeditious entry into mirror-image oligosaccharides, as demonstrated in the synthesis of the unnatural enantiomer of the H-type II blood group determinant trisaccharide (D-Fuc-(alpha1-->2)-L-Gal-(beta1-->4)-L-GlcNAc-beta-OMe). This work illustrates that D-glucose, a common starting material in the synthesis of naturally occurring carbohydrates, can also be used to prepare their mirror-image analogues.

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页码：3391 / 3399

页数：9

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