Efficient and Stereoselective Synthesis of α(2→9) Oligosialic Acids: From Monomers to Dodecamers

被引：57

作者：

Chu, Kuo-Ching ^{[1
]}

Ren, Chien-Tai ^{[1
]}

Lu, Chun-Ping ^{[4
]}

Hsu, Che-Hsiung ^{[1
,2
,3
]}

Sun, Tsung-Hsien ^{[1
]}

Han, Jeng-Liang ^{[1
]}

Pal, Bikash ^{[1
]}

Chao, Tsung-An ^{[1
]}

Lin, Yung-Feng ^{[1
]}

Wu, Shih-Hsiung ^{[4
]}

Wong, Chi-Huey ^{[1
,2
]}

Wu, Chung-Yi ^{[1
,2
]}

机构：

[1] Acad Sinica, Genom Res Ctr, Sect 2, Taipei 115, Taiwan

[2] Acad Sinica, Taiwan Int Grad Program, Taipei 115, Taiwan

[3] Natl Tsing Hua Univ, Inst Bioinformat & Struct Biol, Hsinchu, Taiwan

[4] Acad Sinica, Inst Biol Chem, Taipei 115, Taiwan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 40期

关键词：

block synthesis; glycosylation; oligosaccharides; structure elucidation; synthetic methods; ALPHA-SELECTIVE SIALYLATIONS; ONE-POT SYNTHESIS; SIALIC-ACID; MENINGOCOCCAL POLYSACCHARIDES; CHEMICAL PROPERTIES; ESCHERICHIA-COLI; COLOMINIC ACID; O-SIALYLATION; DONORS; THIOSIALOSIDE;

D O I：

10.1002/anie.201101794

中图分类号：

O6 [化学];

学科分类号：

070301 [无机化学];

摘要：

The chain gang: The α(2→9) dodecasialic acid has been stereoselectively synthesized in 12 steps by using a convergent block synthesis (see scheme). The use of chloroacetyl protecting groups and a phosphate group as a leaving group led to the improvement of the α selectivity of the glycosylation reactions, thus allowing synthesis of oligomers. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9391 / 9395

页数：5

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