Use of carbohydrate derivatives for studies of phosphorus stereochemistry. Part II. Synthesis and configurational assignments of 1,-3,2-oxathiaphosphorinan-2-ones and 1,3,2-dioxaphosphorinan-2-thiones

Abstract

Methyl 2,3-di-O-methyl-4(or 6)-thio-α-D-glucopyranoside (R)- and (S)-4,6-methylphosphonothioates and methyl 2,3-di-O-methyl-α-D-glucopyranoside (R)- and (S)-4,6-methyl-(and phenyl)-phosphonothioates have been prepared by conventional procedures. The corresponding ethyl phosphorothioates are also described. The configuration at phosphorus in the thiolates has been assigned on the basis of n.m.r. and i.r. data. The thioxo-compounds have been correlated chemically with the corresponding phosphates of previously determined configuration. The preparation of methyl 2,3-di-O-methyl-4(and 6)-thio-α-D-glucopyranosides is described.