Unprecedented b-manno type thiodisaccharides with a C-glycosylic function by photoinitiated hydrothiolation of 1-C-substituted glycals

Lázár, László and Juhász, László and Batta, Gyula and Borbás, Anikó and Somsák, László (2017) Unprecedented b-manno type thiodisaccharides with a C-glycosylic function by photoinitiated hydrothiolation of 1-C-substituted glycals. New Journal of Chemistry, 41 (3). pp. 1284-1292. ISSN 1144-0546, ESSN: 1369-9261

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Abstract

Free-radical hydrothiolation of O-peracylated 1-C-(carbamoyl-, methoxycarbonyl- and cyano) substituted glycals with a range of sugar derived thiols gave the corresponding b-manno type 3-deoxy-3-Sdisaccharides with full regio- and stereoselectivity. The configuration of the glycals (arabino vs. lyxo) and the size of the protecting groups had no significant effect on the outcome of the transformations. Formation of by-products was tracked down by LCMS studies and correlated with the electron density of the double bonds to show that the reactions were synthetically useful with a COOMe and especially with a CONH2 group as the 1-C-substituent.

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