Synthesis of a 3‑Thiomannoside

Comba, María B.; Suárez, Alejandra G.; Sarotti, Ariel M.; Mangione, María I.; Spanevello, Rolando A.; Giordano, Enrique D. V.

doi:10.1021/acs.orglett.6b00428.s001

ol6b00428_si_001.pdf (1.45 MB)

Synthesis of a 3‑Thiomannoside

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.