Reactions of the ketone derived from (±)-3,4,5-tri- O-benzyl-1,2- O-isopropylidene- myo-inositol: preparation of racemic derivatives of epi-inositol and of 4- C-methyl- epi- [(±)- iso-laminitol] and 4- C-methyl- myo-inositol [(±)-laminitol]

Oxidation of (±)-3,4,5-tri- O-benzyl-1,2- O-isopropylidene- myo-inositol with the pyridine-SO 3 complex in methyl sulfoxide gave the ketone which was reduced with sodium borohydride to give almost exclusively the corresponding epi-inositol derivative. Reaction of the ketone with diazomethane gave an...

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Bibliographic Details
Published in:Carbohydrate research 1997-03, Vol.299 (1), p.77-83
Main Authors: Gigg, Jill, Gigg, Roy
Format: Article
Language:English
Subjects:
C-Methyl derivatives of myo- and epi-inositol
epi-Inositol
Inosose
iso-Laminitol
Laminitol
Oxirane
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Summary:Oxidation of (±)-3,4,5-tri- O-benzyl-1,2- O-isopropylidene- myo-inositol with the pyridine-SO 3 complex in methyl sulfoxide gave the ketone which was reduced with sodium borohydride to give almost exclusively the corresponding epi-inositol derivative. Reaction of the ketone with diazomethane gave an epoxide which was reduced with lithium aluminium hydride to give a 4- C-methyl- myo-inositol derivative and reaction of the ketone with methyl magnesium iodide gave the isomeric 4- C-methyl- epi-inositol derivative.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(96)00330-8