STEREOSELECTIVE SYNTHESIS OF PROTECTED 5-DEOXY-4,5-DIDEOXY-PENTOSES AND 4-AMINO-4,5-DIDEOXY-PENTOSES VIA NOREPHEDRINE DERIVED OXAZOLIDINES

Catalytic ''anhydrous'' osmylation of the chirally masked 2-alkoxypent -3-enal, 1, takes place with 92:8 diastereomeric ratio. Subsequent fun ctional group manipulations afford enantiopure O-protected 5-deoxy-L-p entoses of the lyxo as well as of the xylo series. Overman rearrangeme nt of the allylic alcohol derived from 1, followed by double bond osmy lation, auxiliary cleavage, and diol acetonation affords a fully prote cted 4-amino-4,5-dideoxy-D-xylose.