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Synthesis of a 3‑Thiomannoside

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journal contribution
posted on 2016-04-07, 12:08 authored by María B. Comba, Alejandra G. Suárez, Ariel M. Sarotti, María I. Mangione, Rolando A. Spanevello, Enrique D. V. Giordano
An efficient and straightforward synthesis of a novel 3-thiomannoside derivative (1,2,4,6-tetra-O-acetyl-3-S-acetyl-3-thio-β-d-manno­pyranoside) was developed starting from levoglucosenone. A xanthate–thiocarbonate exchange under acidic conditions was the key step for the new C–S bond. The product was obtained enantiospecifically in very good overall yield.