Formation and characterization of 5- C-[( R)-(1-acetoxy-ethenyl)phosphinyl]-1,2,4-tri- O-acetyl-5-deoxy-3- O-methyl-β- d-xylopyranose

Abstract

Treatment of 5-deoxy-3- O-methyl-5- C-phosphinyl- d-xylopyranose with acetic anhydride in pyridine gave, along with other products, a peracetylated derivative, to which the title structure was assigned on the basis of 400-MHz, 1H-n.m.r. and high-resolution mass spectra. The previous, 5- C-[( S)-(1-acetoxyethenyl)phosphino] structure, presented for the by-product during the preparation of tri- O-acetyl-5-deoxy-5- C-(methoxyphosphinyl)-3- O-methyl- d- xylopyranoses, is now replaced by the new formulation. Possible structures of other products of the acetylation are discussed. Analysis of the mass spectrum of a sugar analog having a 5-deoxy-5- C-(phosphinyl)- d-xylopyranose ring-system is made.