Preparation of 6,6,1′,1′,6′,6′-hexadeutero sucrose

• Published in: Carbohydrate research Vol. 342; no. 15; pp. 2303 - 2308
• Main Authors: Gouy, Marie-Hélène, Danel, Mathieu, Gayral, Maud, Bouchu, Alain, Queneau, Yves
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 05.11.2007; Elsevier
• Subjects: Aluminum - chemistry; Biochemistry & Molecular Biology; Carbohydrate Conformation; Carbohydrate Sequence; Chemistry; Chemistry, Applied; Chemistry, Organic; Chromatography, High Pressure Liquid; Chromatography, Thin Layer - methods; Cyclic N-Oxides - chemistry; Deuteration; Deuterium - chemistry; Esters; Isotope; Labelled compounds; Life Sciences & Biomedicine; Lithium - chemistry; Models, Chemical; Molecular Sequence Data; Oxidation; Oxygen - chemistry; Physical Sciences; Science & Technology; Sucrose; Sucrose - chemical synthesis; Sucrose - chemistry; TEMPO; Tricarboxylic Acids - chemistry; Uronic acids; Uronic Acids - chemistry; Isotope; Sucrose; Uronic acids; Labelled compounds; Oxidation; Deuteration; TEMPO; uronic acids; deuteration; ACID; oxidation; SUCROCHEMISTRY; isotope; labelled compounds; CATALYST; sucrose; SUGARS; HYDROGEN; NMR; REDUCTION; DEUTERIUM-EXCHANGE; ESTERS
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2007.06.024

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 2O– t-BuOH (to the t-butyl carboxylic ester).