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
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
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