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

Citation
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
Citations number
30
Categorie Soggetti
Chemistry
Journal title
ISSN journal
00165603
Volume
125
Issue
10
Year of publication
1995
Pages
505 - 507
Database
ISI
SICI code
0016-5603(1995)125:10<505:SSOP5A>2.0.ZU;2-M
Abstract
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.