Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols

T Ghosh, A Santra, AK Misra

Index: Ghosh, Tamashree; Santra, Abhishek; Misra, Anup Kumar Beilstein Journal of Organic Chemistry, 2013 , vol. 9, p. 974 - 982

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Citation Number: 5

Abstract

Abstract A series of glycosyl hemiacetal derivatives have been transformed into thioglycosides and glycosyl thiols in a one-pot two-step reaction sequence mediated by Appel reagent (carbon tetrabromide and triphenylphosphine). 1, 2-trans-Thioglycosides and β-glycosyl thiol derivatives were stereoselectively formed by the reaction of the in situ generated glycosyl bromides with thiols and sodium carbonotrithioate. The reaction ...