Synthesis of the C-glycoside of α-d-mannose-(1 → 6)-d-myo-inositol?

Organic & Biomolecular Chemistry Pub Date: 2013-08-30 DOI: 10.1039/C3OB41337C

Abstract

The dimannosylatedinositol pseudotrisaccharide phospholipid of the lipoarabinomannan (LAM) component of the mycobacterial cell wall has attracted interest as a therapeutic target because of its uniqueness to mycobacteria, its assembly at an early stage in LAM biosynthesis and the immunological activity of oligosaccharides containing this subunit. Accordingly, analogues of this pseudotrisaccharide, α-D-mannose-(1 → 2)-α-D-mannose-(1 → 6)-D-myo-inositol are of interest as mechanistic probes and drug leads. C-glycosides are of special interest because of their hydrolytic stability and conformational differences compared to O-glycosides. Herein, as a prelude to C-glycoside analogues of this pseudotrisaccharide, we describe the synthesis of the C-glycoside of α-D-mannose-(1 → 6)-D-myo-inositol. The synthetic strategy centers on the elaboration of a C1-linked glycal-inositol, the glycone segment of which is assembled via an oxocarbenium ion cyclization on a thioacetal-enol ether precursor that originates from “glycone” and “aglycone” components.

Graphical abstract: Synthesis of the C-glycoside of α-d-mannose-(1 → 6)-d-myo-inositol
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