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À propos de : Conversion of Glucosamine to Galactosamine and AllosamineDerivatives: Control of Inversions of Stereochemistry at C-3 andC-4        

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  • Conversion of Glucosamine to Galactosamine and AllosamineDerivatives: Control of Inversions of Stereochemistry at C-3 andC-4
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  • The reactions of sodium benzoate with a series of trimesylates derived from glucosamine havebeen examined in an attempt to gain facile access to galactosamine analogues. Trimesylate 17, inwhich the amino group was protected as a phthalimide, underwent double displacement at positions4 and 6 to give the dibenzoate 18 with the desired galactosamine configuration. In contrast,trimesylates 21 and 27, in which the amino groups were protected as acetamides, unexpectedlyunderwent double displacement at positions 3 and 6, giving products 22 and 28, respectively, withallosamine configurations.
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