TUD Organische Chemie

Immel

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Practical Synthesis of β-D-Xyl-(1→2)-β-D-Man-(1→4)-α-D-Glc-OMe, a Trisaccharide Component of the Hyriopsis Schlegelii Glycosphingolipid

Frieder W. Lichtenthaler, Thomas Schneider-Adams, and Stefan Immel

J. Org. Chem. 1994, 59, 6735-6738.

By employing the readily accessible 3,4,6-tri-O-benyzl-α-D-arabino-hexosyl bromide (1) as an indirect, β-specific mannosyl donor, a practical three-step synthesis was elaborated for methyl xylosyl-β(1→2)-mannosyl-β(1→4)-glucoside (11), a trisaccharide component of the Hyriopsis Schlegelii ceramide oligosaccharides. Key steps were the silver aluminosilicate-induced, β-specific glycosidation of 1 with methyl 2,3,6-tri-O-benyzl-α-D-glucoside and the silver triflate-promoted β-xylosylation with 2,3,4-tri-O-benyzl-α-D-xylosyl bromide. The over-all yield amounted to a satisfactory 47%.