ChemInform Abstract: Alkylation and Acylation of Phenylthio-2,3-dideoxyhex-2-enopyranosides at the Anomeric Centre by Polarity Inversion.

ChemInform Abstract

Substitution of the tri-O-acetyl-D-glucal (I) with thiophenol (II) produces the dideoxyenopyranosides (III). Hydrolysis of the α-derivative (IIIa) and subsequent protection give the acetal (VI) which undergoes cleavage on attempted metalation, forming the thiol ester (VII). The benzyl ether (VIII) is transformed into the C-1-derivatives (IX) - (XII) by metalation and subsequent reaction withelectrophiles such as acetone, ethyl acetate, benzaldehyde, and dimethyl carbonate.