Neighboring-Group Participation by C-2 Ether Functions in Glycosylations Directed by Nitrile Solvents

被引：65

作者：

Chao, Chin-Sheng ^{[1
]}

Lin, Ching-Yu ^{[1
]}

Mulani, Shaheen ^{[1
]}

Hung, Wei-Cheng ^{[1
]}

Mong, Kwok-kong Tony ^{[1
]}

机构：

[1] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu, Taiwan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 43期

关键词：

arabinans; glycosylation; neighboring-group effects; nitrile solvents; oligosaccharides; BETA-SELECTIVE GLYCOSYLATION; STEREOSELECTIVE-SYNTHESIS; TUBERCULOSIS; GLYCOSIDES; ARABINOFURANOSIDES; OLIGOSACCHARIDES; ACCEPTORS; DONOR;

D O I：

10.1002/chem.201100732

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ether-protecting functions at C-2 hydroxy groups have been found to play participating roles in glycosylations when the reactions are conducted in nitrile solvent mixtures. The participation mechanism is based on intramolecular interaction between the lone electron pair of the oxygen atom of the C-2 ether function and the nitrile molecule when they are positioned in a cis configuration. A 1,2-cis glycosyl oxazolinium intermediate is formed. This participation, in conjunction with the anomeric effect of the glycosyl donor, confers high 1,2-trans selectivities on glycosylations. Further application of this concept has led to efficient preparations of alpha-(1 -> 5)-arabinan oligomers.

引用

页码：12193 / 12202

页数：10

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