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Stereodivergent Syntheses of altro and manno Stereoisomers of 2‐Acetamido‐1,2‐dideoxynojirimycin
Author(s) -
de la Fuente Alex,
Verdaguer Xavier,
Riera Antoni
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701282
Subject(s) - chemistry , stereoselectivity , epimer , enantiomer , stereochemistry , bicyclic molecule , amine gas treating , carbamate , combinatorial chemistry , organic chemistry , catalysis
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 asymmetric epoxidation 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.