Chemo-enzymatic synthesis of the azasugars 1, 4-dideoxyallonojirimycin and 1, 4-dideoxymannojirimycin
M Venkataiah, G Reddipalli, LS Jasti…
Index: Venkataiah, Mallam; Reddipalli, Gowrisankar; Jasti, Lakshmi Swarnalatha; Fadnavis, Nitin W. Tetrahedron Asymmetry, 2011 , vol. 22, # 20-22 p. 1855 - 1860
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Citation Number: 13
Abstract
The enzymatic resolution of the N-phenylacetyl derivative of racemic homoserine lactone with penicillin G acylase immobilized on Eupergit C gave (R)-(+)-α-amino-γ-butyrolactone and (S)-(−)-α-N-phenylacetamido-γ-butyrolactone in high enantiomeric purity (ee> 99%) and 46–47% yields for each enantiomer. The enantiomers were converted into azasugars 1, 4- dideoxyallonojirimycin and 1, 4-dideoxymannojirimycin using Wittig olefination, catalytic ...
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