# name
Stereodivergent syntheses of altro and manno stereoisomers of 2-acetamido-1,2-dideoxynojirimycin

# metadata.dc.description.abstract[].value
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.

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European Journal of Organic Chemistry, 2017, vol. 2017, num. 47, p. 7179-7185

# metadata.dc.source[].value
Articles publicats en revistes (Química Inorgànica i Orgànica)

# metadata.dc.title[].value
Stereodivergent syntheses of altro and manno stereoisomers of 2-acetamido-1,2-dideoxynojirimycin