G. Poli et al., STEREOSELECTIVE SYNTHESIS OF PROTECTED 5-DEOXY-4,5-DIDEOXY-PENTOSES AND 4-AMINO-4,5-DIDEOXY-PENTOSES VIA NOREPHEDRINE DERIVED OXAZOLIDINES, Gazzetta chimica italiana, 125(10), 1995, pp. 505-507
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.