New efficient synthesis of a biosynthetic precursor of lipid A

被引：31

作者：

Oikawa, M ^{[1
]}

Wada, A ^{[1
]}

Yoshizaki, H ^{[1
]}

Fukase, K ^{[1
]}

Kusumoto, S ^{[1
]}

机构：

[1] OSAKA UNIV, GRAD SCH SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1997年 / 70卷 / 06期

关键词：

D O I：

10.1246/bcsj.70.1435

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A biosynthetic precursor of lipid A has been synthesized by an improved efficient method. Two appropriately modified acyl-substituted glucosamine units were synthesized from D-glucosamine using (R)-3-(benzyloxy)tetradecanoic acid and then coupled by the Lewis acid-promoted glycosidation via the corresponding trichloroacetimidate. Glycosyl phosphorylation and hydrogenolytic deprotection, followed by purification by liquid-liquid partition chromatography, afforded the target compound in 2.9% total yield through 13 steps from N-Troc-D-glucosamine.

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页码：1435 / 1440

页数：6

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