CHEMOENZYMATIC SYNTHESIS OF GLYCOSYLATED ENANTIOMERICALLY PURE 4-PENTENE 1,2-DIOL AND 1,3-DIOL DERIVATIVES

Authors
Citation
F. Bien et T. Ziegler, CHEMOENZYMATIC SYNTHESIS OF GLYCOSYLATED ENANTIOMERICALLY PURE 4-PENTENE 1,2-DIOL AND 1,3-DIOL DERIVATIVES, Tetrahedron : asymmetry, 9(5), 1998, pp. 781-790
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
ISSN journal
09574166
Volume
9
Issue
5
Year of publication
1998
Pages
781 - 790
Database
ISI
SICI code
0957-4166(1998)9:5<781:CSOGEP>2.0.ZU;2-P
Abstract
1-Dimethylthexylsiloxy-2-chloroacetoxy-4 2 and 1-dimethylthexylsiloxy- 3-chloroacetoxy-4-pentene 3 were saponified with Pseudomonas lipase to give (R)-1-dimethylthexylsiloxy-4-pentene-2-ol (ee=99%) and (S)-2 (ee =99%) and (S)-1-dimethylthexylsiloxy-4-pentene-3-ol (ee=99%) and (R)-3 (ee=98%), respectively. All enantiomers were chemically transformed i nto the corresponding enatiomerically pure 2-benzoyloxy-4-pentene-1-ol s 8 and 3-benzoyloxy-4-pentene-1-ols 14, respectively. Mannosylation o f (R)-8 and (S)-14 with 2,3,4,6-tetra-O-benzoyl-a-D-mannopyranosyl tri chloroacetimidate afforded the corresponding mannopyranosides. (C) 199 8 Elsevier Science Ltd. All rights reserved.