Convenient Preparation of 2-Deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl Chloride

Abstract

By using acetyl chloride as HCl generator, the procedure for the Hoffer preparation of the α-chloro sugar 4a was significantly improved. The α-configuration of the chloro atom was confirmed by using NOE measurement. Sequential transformation of 4a to the β-anomer and to the furfuryl derivative 6 was studied.

Notes

In these conditions, the furanoside epimers 3 seem to be the major compounds if not exclusive. The pyranosides 5 were not observed in crude mixture by ¹H NMR.