C-methylation of sucrose: synthesis of 6- and 6′- C-methylsucrose

2,3,4,6,1′,3′,4′-Hepta- O-benzylsucrose, obtained by acid-catalysed hydrolysis of the 6′- O-trityl derivative, was oxidised with the Pfitzner-Moffatt reagent and the product was alkylated with methylmagnesium iodide. Removal of the protecting groups then gave a mixture of diastereomers, namely 7-deo...

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Bibliographic Details
Published in:Carbohydrate research 1986-05, Vol.148 (2), p.279-285
Main Authors: Toufeili, Imad A., Dziedzic, Stanley Z., Rathbone, Elner B.
Format: Article
Language:English
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Summary:2,3,4,6,1′,3′,4′-Hepta- O-benzylsucrose, obtained by acid-catalysed hydrolysis of the 6′- O-trityl derivative, was oxidised with the Pfitzner-Moffatt reagent and the product was alkylated with methylmagnesium iodide. Removal of the protecting groups then gave a mixture of diastereomers, namely 7-deoxy-β- d- altro and -α- l- galacto-hept-2-ulofuranosyl α- d-glucopyranoside. Application of this reaction sequence to 2,3,4,1′,3′,4′,6′-hepta- O-benzylsucrose afforded β- d-fructo-furanosyl 7-deoxy- dl- glycero-α- d- gluco-heptopyranoside.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(00)90395-1