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2005
Carbohydrates
U 0500
Synthesis of Thioglycosides by Tetrathiomolybdate-Mediated Michael Additions
Masked Thiolates. — Thioglycosides are prepared in excellent yields under neutral
14- 195 of
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. J. Org. Chem. 2004, 23, 4809-4815; Dep. Org.
Chem., Indian Inst. Sci., Bangalore 560 012, India; Eng.) — Klein
2005
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