Beilstein J. Org. Chem.2013,9, 974–982, doi:10.3762/bjoc.9.112
thiols in a one-pot two-step reaction sequence mediated by Appelreagent (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 conditions are reasonably simple and yields were very good.
Keywords: Appelreagent; carbon tetrabromide; glycosyl hemiacetal; glycosyl thiol; thioglycoside; triphenylphosphine; Introduction
Thioglycosides (1-thiosugar) are widely used glycosyl donors in glycosylation reactions [1
extension of the earlier report [43], it was envisioned that the treatment of a stable glycosyl hemiacetal derivative with Appelreagent (carbon tetrabromide (CBr4) and triphenylphosphine (PPh3)) [44] could generate the glycosyl bromide in situ, [45][46] which, on reaction with thiol or sodium
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Graphical Abstract
Scheme 1:
Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and β-...