Please use this identifier to cite or link to this item: http://hdl.handle.net/2445/119330
Title: Stereodivergent syntheses of altro and manno stereoisomers of 2-acetamido-1,2-dideoxynojirimycin
Author: Fuente Cebrián, Àlex de la
Verdaguer i Espaulella, Xavier
Riera i Escalé, Antoni
Keywords: Disseny de medicaments
Inhibidors enzimàtics
Drug design
Enzyme inhibitors
Issue Date: 21-Dec-2017
Publisher: Wiley-VCH
Abstract: A stereoselective synthesis of 2-acetamido-1,2-dideoxyaltronojirimycin (8) and its manno epimer 9 is described. The synthetic approach is based on key bicyclic carbamate 7, which is easily accessible with high enantiomeric purity on a multigram scale by Sharpless asym. epoxidn. of 1,4-pentadien-3-ol or 2,4-pentadien-1-ol. This procedure completes an efficient stereodivergent approach to five isomers of 2-acetamido-1,2-dideoxyiminosugars in high overall yields starting from the same key intermediate 7. The approach described in this paper is based on control of the stereoselectivity of the sulfite ring-opening reaction to give retention of configuration through anchimeric assistance from the endocyclic amine.
Note: Versió postprint del document publicat a: https://doi.org/10.1002/ejoc.201701282
It is part of: European Journal of Organic Chemistry, 2017, vol. 2017, num. 47, p. 7179-7185
URI: http://hdl.handle.net/2445/119330
Related resource: https://doi.org/10.1002/ejoc.201701282
ISSN: 1434-193X
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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