Efficient Large Scale Syntheses of 3-Deoxy-D-manno-2-octulosonic acid (Kdo) and Its Derivatives

被引：23

作者：

Peng, Yingle ^{[1
]}

Dong, Jie ^{[1
]}

Xu, Fangyuan ^{[1
]}

Liu, Aiyun ^{[1
]}

Zhang, Qi ^{[1
]}

Chai, Yonghai ^{[1
]}

机构：

[1] Shaanxi Normal Univ, Sch Chem & Chem Engn, Xian 710119, Shaanxi, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 10期

基金：

中国国家自然科学基金;

关键词：

RING-CLOSING METATHESIS; C-H BONDS; D-MANNOSE; LIPOPOLYSACCHARIDE BIOSYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CHEMICAL-SYNTHESIS; 2-DEOXY ANALOG; SYNTHETASE; 2-DEOXY-BETA-KDO; ROUTE;

D O I：

10.1021/acs.orglett.5b00901

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method to rapidly synthesize 3-deoxy-D-manno-2-octulosonic acid (Kdo) and its derivatives in large scale has been developed. Starting from D-mannose, the di-O-isopropylidene derivative of Kdo ethyl ester was prepared in three steps on a scale of more than 40 g in one batch in an overall yield of 75-80% without any intermediate purification. Kdo, Kdo glycal, and 2-acetylated Kdo ester were synthesized quickly in high yield from a di-O-isopropylidene derivative of Kdo ethyl ester. 2-Deoxy-beta-Kdo ester was obtained with high stereoselectivity via the epimerization of the alpha-isomer using t-BuOH as a proton source.

引用

页码：2388 / 2391

页数：4

共 50 条

[1] SYNTHESIS OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO)
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