Preparation of 6,6,1',1',6',6'-hexadeutero sucrose.
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).
Gouy
Marie-Hélène
MH
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.
Danel
Mathieu
M
Gayral
Maud
M
Bouchu
Alain
A
Queneau
Yves
Y
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*
D003497:Cyclic N-Oxides; D004952:Esters; D014233:Tricarboxylic Acids; D014574:Uronic Acids; D013395:Sucrose; D008094:Lithium; D003903:Deuterium; D000535:Aluminum; D010100:Oxygen; C003959:TEMPO