CHEMOENZYMATIC SYNTHESIS OF FLUORINATED CARBOHYDRATES - 2-DEOXY-2-FLUORO-D-GLUCOSE AND 5-DEOXY-5-FLUORO-MANNO-GAMMA-LACTOL

Authors
YAN FY NGUYEN BV YORK C HUDLICKY T
Citation
Fy. Yan et al., CHEMOENZYMATIC SYNTHESIS OF FLUORINATED CARBOHYDRATES - 2-DEOXY-2-FLUORO-D-GLUCOSE AND 5-DEOXY-5-FLUORO-MANNO-GAMMA-LACTOL, Tetrahedron, 53(34), 1997, pp. 11541-11548
Citations number
50
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
34
Year of publication
1997
Pages
11541 - 11548
Database
ISI
SICI code
0040-4020(1997)53:34<11541:CSOFC->2.0.ZU;2-0
Abstract
Two fluorinated hexoses were prepared from optically active cis-diols 1, which were obtained by microbial oxidation of the corresponding hal obenzenes with E. coli JM109 (pDTG 601). The stereochemistry of the pr oducts was controlled by careful introduction of fluorine onto the per iphery of the cis-diols via opening of epoxides with tetrabutylphospho niumfluoride dihydrofluoride (TBPF-DF). Oxidative cleavage of the cycl ohexene skeleton followed by reductive cyclization led to the fluorina ted hexoses. (C) 1997 Elsevier Science Ltd.