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Diphenylmethylation of carbohydrate hydroxyl groups by the reaction with diazo(diphenyl)methane

Jackson, Graham ; Jones, Haydn F. ; Petursson, Sigthor ; Webber, John M.

Carbohydrate research, 1982-01, Vol.102 (1), p.147-157 [Periódico revisado por pares]

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Título:
Diphenylmethylation of carbohydrate hydroxyl groups by the reaction with diazo(diphenyl)methane
Autor: Jackson, Graham ; Jones, Haydn F. ; Petursson, Sigthor ; Webber, John M.
É parte de: Carbohydrate research, 1982-01, Vol.102 (1), p.147-157
Descrição: Diphenylmethylation of carbohydrate hydroxyl groups may be effected by the thermal reaction with diazo(diphenyl)methane in the absence of catalysts. Migration of the labile ester groups of methyl 2,3,4-tri- O-acetyl-α- d-glucopyranoside and 3- O-benzoyl-1,2- O-isopropylidene-α- d-glucofuranose does not occur during diphenylmethylation by this procedure. The diphenylmethyl group may be readily removed by catalytic hydrogenolysis, and is sufficiently acid-stable to enable the selective hydrolysis of acetal groups. Its use as an O-4 protecting-group and as a non-participating O-2 protecting-group in α-glycoside synthesis has been demonstrated in syntheses of methyl 2,3,6-tri- O-methyl-α- d-glucopyranoside and kojibiose octa-acetate, respectively.
Editor: Elsevier Ltd
Idioma: Inglês

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