Synthesis and structure assignment of the diastereoisomeric 1,2-O-cyclohexylidene-α-D-xylofuranose 3,5-O-methylphosphonates and the related thiono- and selenono-phosphonates

Abstract

The diastereoisomeric 1,2-O-cyclohexylidene-α-D-xylofuranose 3,5-O-methylphosphonates have been synthesized as a mixture and separated by chromatography to give the pure (R_P) and (S_P) forms. The related thiono- and setenono-phosphonates have also been obtained. Their ¹³C, ¹H, ³¹P, and ⁷⁷Se NMR spectra are discussed and NOE experiments have been used to determine the chirality at phosphorus.