title: Preparation of 6,6,1',1',6',6'-hexadeutero sucrose.
abstract: The preparation of 6,6,1',1',6',6'-hexadeutero sucrose is reported. The synthesis is based on a triple oxidation of a protected sucrose 6,1',6'-triol to the corresponding 6,1',6'-tricarboxylic acid or ester, followed by reduction with lithium aluminium deuteride. This triple oxidation could be achieved either using cat. TEMPO-NaOCl (to the acid) or PDC-Ac(2)O-t-BuOH (to the t-butyl carboxylic ester).
authors.affiliation: Institut de Chimie et de Biochimie Moléculaires et Supramoléculaires, UMR 5246, CNRS; Université de Lyon; Université Lyon 1; INSA-Lyon; CPE-Lyon; Laboratoire de Chimie Organique, INSA-Lyon, Bât. Jules Verne, 20 Avenue Albert Einstein, Villeurbanne, France.
authors.forename: Marie-Hélène
authors.initials: MH
authors.lastname: Gouy
authors.forename: Mathieu
authors.initials: M
authors.lastname: Danel
authors.forename: Maud
authors.initials: M
authors.lastname: Gayral
authors.forename: Alain
authors.initials: A
authors.lastname: Bouchu
authors.forename: Yves
authors.initials: Y
authors.lastname: Queneau
mesh_terms: D000535:Aluminum / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer / Q000379:methods; D003497:Cyclic N-Oxides / Q000737:chemistry*; D003903:Deuterium / Q000737:chemistry; D004952:Esters; D008094:Lithium / Q000737:chemistry; D008956:Models, Chemical; D008969:Molecular Sequence Data; D010100:Oxygen / Q000737:chemistry*; D013395:Sucrose / Q000138:chemical synthesis / Q000737:chemistry*; D014233:Tricarboxylic Acids / Q000737:chemistry; D014574:Uronic Acids / Q000737:chemistry*
chemical_list: D003497:Cyclic N-Oxides; D004952:Esters; D014233:Tricarboxylic Acids; D014574:Uronic Acids; D013395:Sucrose; D008094:Lithium; D003903:Deuterium; D000535:Aluminum; D010100:Oxygen; C003959:TEMPO