ASYMMETRIC-SYNTHESIS OF 2-DEOXY-2-FLUORO-GAMMA-ALDONOLACTONES AND THEIR CONVERSION TO 2-DEOXY-2-FLUOROPENTOSES

Authors
DAVIS FA QI HY
Citation
Fa. Davis et Hy. Qi, ASYMMETRIC-SYNTHESIS OF 2-DEOXY-2-FLUORO-GAMMA-ALDONOLACTONES AND THEIR CONVERSION TO 2-DEOXY-2-FLUOROPENTOSES, Tetrahedron letters, 37(25), 1996, pp. 4345-4348
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
25
Year of publication
1996
Pages
4345 - 4348
Database
ISI
SICI code
0040-4039(1996)37:25<4345:AO2AT>2.0.ZU;2-7
Abstract
2-Fluoro-2-deoxy-gamma-xylonic and -lyxonic lactones, 7a and 7b, were prepared via the diastereoselective fluorination of the alpha,beta-uns aturated chiral imide 5 followed by dihydroxylation. Lactones 7a and 7 b were converted to 2-deoxy-2-fluoro-xylo-D-pyranose (1) and 2-deoxy-2 -fluoro-lyxo-L-pyranose (2) by reduction and deprotection. Copyright ( C) 1996 Elsevier Science Ltd.