Synthesis of Thioglycosides by Tetrathiomolybdate‐Mediated Michael Additions of Masked Thiolates.

Abstract

Synthesis of Thioglycosides by Tetrathiomolybdate-Mediated Michael Additions of MaskedThiolates. -Thioglycosides are prepared in excellent yields under neutral conditions by use of tetrathiomolybdates as sulfur-transfer reagents. Sugar halides give by reaction with the molybdates sugar disulfides, which then undergo reductive cleavage in situ to afford the corresponding thiolates. The subsequent Michael addition with alkenes provides the desired thioglycosides. The successful application of the method in aqueous medium is demonstrated. Some inter-and intramolecular diastereoselective variants of the method are also presented. In the case of substrate (XV), the reaction is unsuccessful and a dimeric disulfide is formed. -(SRIDHAR, P. R.; PRABHU, K. R.; CHANDRASEKARAN*, S.; Eur.

Unexpected matrix interactions in liquid secondary ion mass spectrometry of two pyranosyl mercaptans

“…(a)). The latter ion was the only one observed in the ESI mass spectrum of 2a . It was easy to recognize in the LSIMS spectra with thioglycerol of 2a and 5a the cationized molecules at m/z 387, 493 and 749 (Figs.…”