20220805 Lowary TL paper photo

A De Novo Route to 3,6-Dideoxy Sugars

A De Novo Route to 3,6-Dideoxy Sugars

Org Lett. 2022 Aug 5; 24(30):5614-5618. Epub 2022 Jul 26.
doi: 10.1021/acs.orglett.2c02349

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Yang S, Chu CJ, Lowary TL*


We report the de novo asymmetric synthesis of the 3,6-dideoxy sugars abequose, paratose, and tyvelose from 2-acetylfuran. Conversion of this readily available ketone to a pyranone derivative was followed by transformation to either an α- or β-glycoside via diasteroselective acylation. Michael addition at C2 controlled primarily by the C1 configuration in the glycoside produced 3,6-dideoxy-4-keto sugars, which could be reduced and converted to either fully deprotected monosaccharides or to immediate precursors of glycosyl donors.