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.
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页码：2388 / 2391
页数：4
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