title: Desymmetrization of 2,4,5,6-tetra-O-benzyl-D-myo-inositol for the synthesis of mycothiol.
abstract: An efficient chemical synthesis of mycothiol involving the regioselective ketopinyl desymmetrization of 2,4,5,6-tetrabenzylated D-myo-inositol as the key step is described. Together with a highly α-stereoselective D-glucosaminylation, the whole procedure was accomplished in eight steps with an overall yield of 40%.
authors.affiliation: Genomics Research Center, Academia Sinica, 128 Sec.2 Academia Road, Taipei 115, Taiwan.
authors.forename: Chuan-Chung
authors.initials: CC
authors.lastname: Chung
authors.forename: Medel Manuel L
authors.initials: MM
authors.lastname: Zulueta
authors.forename: Laxmansingh T
authors.initials: LT
authors.lastname: Padiyar
authors.forename: Shang-Cheng
authors.initials: SC
authors.lastname: Hung
mesh_terms: D000818:Animals; D001593:Benzyl Compounds / Q000737:chemistry*; D003545:Cysteine / Q000138:chemical synthesis* / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007295:Inositol Phosphates / Q000138:chemical synthesis; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C568737:2,4,5,6-tetra-O-benzyl-D-myo-inositol; D001593:Benzyl Compounds; D006020:Glycopeptides; D007295:Inositol Phosphates; C089265:mycothiol; D007294:Inositol; D003545:Cysteine