Synthesis of oligosaccharide fragments of mannosylated lipoarabinomannan from Mycobacterium tuberculosis

V Subramaniam, TL Lowary

Index: Subramaniam, Vinodhkumar; Lowary, Todd L. Tetrahedron, 1999 , vol. 55, # 19 p. 5965 - 5976

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Citation Number: 27

Abstract

The synthesis of three mannosyl-arabinosides 4–6 found as terminal epitopes of mannosylated lipoarabinomannan (ManLAM) from Mycobacterium tuberculosis is reported. A key step in the synthesis of the required protected octyl β-d-arabinofuranoside derivative 7 involved glycosylation of octanol by 5-O-acetyl-2, 3-di-O-benzyl-α-d-arabinofuranosyl chloride (12) in the absence of a promoter. The sequential addition of the mannopyranose ...