Synthesis of a pentasaccharide fragment of Polysaccharide II of Mycobacterium tuberculosis

V Pozsgay, JB Robbins

Index: Pozsgay, Vince; Robbins, John B. Carbohydrate Research, 1995 , vol. 277, # 1 p. 51 - 66

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Citation Number: 12

Abstract

Stereocontrolled, stepwise synthesis of decyl glycosides of α-(1→ 2)-linked di-to pentaglucosides (1–5) is described; these constitute fragments of Polysaccharide II of Mycobacterium tuberculosis. Phenyl 3, 4, 6-tri-O-acetyl-2-O-benzyl-1-thio-α-d- glucopyranoside (7) was used as the single key intermediate, obtained from 1, 3, 4, 6-tetra-O- acetyl-2-O-benzyl-β-d-glucopyranose (6) and PhSSiMe3. Halogenolysis of 7 afforded the ...