Stereodivergent Syntheses of altro and manno Stereoisomers of 2‐Acetamido‐1, 2‐dideoxynojirimycin. Issue 47 (21st December 2017)

• Record Type: Journal Article
• Authors: de la Fuente, Alex; Verdaguer, Xavier; Riera, Antoni
• Is Part Of: European journal of organic chemistry. Issue 47(2017)
• Page Start: 7179
• Page End: 7185
• Publication Date: 2017-12-21
• Subjects: Total synthesis -- Carbohydrates -- Iminosugars -- Asymmetric synthesis -- Neighboring‐group effects; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701282
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A stereoselective synthesis of 2‐acetamido‐1, 2‐dideoxyaltronojirimycin (8 ) and its manno epimer9 is described. The synthetic approach is based on key bicyclic carbamate7, 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 intermediate7 . 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. Abstract : The altro and manno isomers (8 and9 ) of 2‐acetamido‐1, 2‐dideoxynojirimycin have been synthesized from key intermediate7 . The key step was the stereoselective sulfite ring‐opening with retention of configuration due to the anchimeric effect of the endocyclic amine.