Approaches to the Syntheses of 2- and 3-Phosphonomethyl Derivatives of Arabinose Via Pentacovalent Oxaphospholene Methodology

Abstract

Approaches to the syntheses of 2- and 3-phosphonomethyl derivatives of arabinose via pentacovalent oxaphospholene methodology are outlined. Condensation of the requisite pentacovalent oxaphospholenes with either a mono-protected glyoxal derivative or glyceraldehyde acetonide were highly stereoselective, producing the syn aldol product as the major isomer in both cases. The reduction of 4a to the diol did not give the expected stereoselectivity. Stereochemical correlation of 5 and 6 were via the carbonates.

Keywords::

• pentacovalent oxaphospholene
• arabinose
• phosphonate analogs
• KDO