MASS SPECTRA OF PERACETYLATED DERIVATIVES OF SUGAR ANALOGUES HAVING PHOSPHORUS IN THE HEMIACETAL RING

Abstract

The first, detailed analysis of the mass spectra of the title compounds having a pyranoid or furanoid ring was carried out. The molecular-ion intensities of these phosphorus sugars were shown to be higher compared to the oxygen analogues, thus permitting accurate mass measurement. The main fragmentation pathway was the consecutive loss of the substituents from ring carbon atoms and C-6 (the A series of fragmentation), leading to the formation of 1,2-dihydro-λ⁵-phosphorin or -phosphole oxide derivatives. Possible degradation pathways of the phosphorus-containing ring to acyclic fragments are also discussed. These findings are considered to be of use in structural analysis of these phosphorus sugars.