title: Regio- and stereocontrolled selective debenzylation and substitution reactions of C-2 formyl glycals. Application in the synthesis of constrained beta-sugar amino acids.
abstract: O-Benzyl-protected C-2 formyl glycals are regioselectively deprotected and acetylated first at C-3 and then at C-6 upon treatment with a ZnCl2-Ac2O-AcOH reagent combination. Treatment of the thus-obtained C-3 acetate with various nucleophiles leads to substitution at C-3 with retention of stereochemistry in the galactal series, whereas mixed results were obtained with glucal-derived compounds. Two of the azido-substituted products were converted into the corresponding beta-sugar amino acids.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India.
authors.forename: Girish K
authors.initials: GK
authors.lastname: Rawal
authors.forename: Shikha
authors.initials: S
authors.lastname: Rani
authors.forename: Nitee
authors.initials: N
authors.lastname: Kumari
authors.forename: Yashwant D
authors.initials: YD
authors.lastname: Vankar
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D002241:Carbohydrates; D006027:Glycosides