Large-scale synthesis of 6-deoxy-6-sulfonatomethyl glycosides and their application for novel synthesis of a heparinoid pentasaccharide trisulfonic acid of anticoagulant activity

• Three 6-sulfonatomethyl α-glucosides were prepared in ten-gram-scales.
• They were obtained by reactions of 6-O-triflates with α-lithio methanesulfonate ester.
• Chemoselective glycosylations of 6-C-sulfonatomethyl donors were studied.
• An anticoagulant pentasaccharide trisulfonic acid was gained via a [2+3] synthesis.

Multigram-scale syntheses of three 6-deoxy-6-sulfonatomethyl α-glucosides were accomplished via reactions of the corresponding primary triflate derivatives with the lithiated ethyl methanesulfonate. Chemoselective glycosylation reactions of different 6-C-sulfonatomethyl glucoside donors were studied. The sulfonic acid-containing building blocks were utilised in a novel [2+3] block synthesis of a trisulfonic acid isoster of the anticoagulant pentasaccharide idraparinux.

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