Chemistry of oxo-sugars. (2). Regio- and stereo-selective synthesis of methyl D-hexopyranosiduloses and identification of their forms existing in solutions
Sixteen oxo derivatives of methyl D-hexopyranosides with various regio-and stereo-chemistries were selectively synthesized by direct oxidation of non-protected methyl glycosides by the bistributyltin oxide-bromine method or by oxidation of partially protected glycosides followed by deprotection. The forms of these oxoglycosides existing in pyridine-d5 and in H2O (D2O) were investigated by means of 13C-NMR spectroscopy, and it was found that interconversion between oxo and hydrate forms of oxoglycosides readily takes place.
Liu,Sato,Tsuda
p. 491 - 501
(2007/10/02)
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