N-pentenyl glycoside methodology in the stereoselective construction of the tetrasaccharyl cap portion of Leishmania lipophosphoglycan

被引：38

作者：

Arasappan, A ^{[1
]}

FraserReid, B ^{[1
]}

机构：

[1] DUKE UNIV,PAUL M GROSS CHEM LAB,DURHAM,NC 27708

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 07期

关键词：

D O I：

10.1021/jo9520102

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient and high yielding stereoselective assembly of the tetrasaccharyl cap region of the lipophosphoglycan from the protozoan parasite Leishmania using the n-pentenyl glycoside protocol is described in this paper. Both convergent and linear syntheses lead to the protected tetrasaccharide 14; however, the convergent assembly is more efficient in terms of product recovery. Regioselective reductive cleavage of benzylidene acetal 4 with triethylsilane-trifluoroacetic acid system liberates the required C-4 OH in excellent yield, without affecting the resident chloroacetate functionality.

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页码：2401 / 2406

页数：6

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