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Synthesis of a 3-Thiomannoside

2016; American Chemical Society; Volume: 18; Issue: 8 Linguagem: Inglês

10.1021/acs.orglett.6b00428

1523-7060

María B. Comba, Alejandra G. Suárez, Ariel M. Sarotti, María I. Mangione, Rolando A. Spanevello, Enrique David Victor Giordano,

Synthesis of Organic Compounds

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.