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Synthesis of 4-C-sulfoaminosugar derivatives: isomerization of 4-C-sulfogalactosamine to its gluco epimer by José G. Fernández-Bolaños; Salud Garcı́a; José Fernández-Bolaños; Ma Jesús Diánez; Ma Dolores Estrada; Amparo López-Castro; Simeón Pérez-Garrido is a Chemistry article available to read on EtoBox.
What is Synthesis of 4-C-sulfoaminosugar derivatives: isomerization of 4-C-sulfogalactosamine to its gluco epimer about?
Methyl 2-benzamido-3,6-di-O-benzoyl-2,4-dideoxy-a-D-glucopyranoside-4-C-sulfonate sodium salt 9 and its galacto epimer 10 were prepared by oxidation with hydrogen peroxide in acetic acid of methyl 4-S-acetyl-2-benzamido-3,6-di-O-benzoyl-2-deoxy-4-thio-a-D-glucopyranoside 7 and its galacto epimer 8, respectively. The 4-thioglucoside 7 was prepared from methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-a-D-glucopyranoside by double inversion through triflation, inversion at C-4 with NaNO 2 , triflation of the resulting methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-a-D-galactopyranoside, followed by displacement with potassium thioacetate. Deacylation of 9 with refluxing aqueous sodium hydroxide followed by deionisation yielded methyl 2-amino-2,4-dideoxy-a-D-glucopyranoside-4-C-sulfonic acid 11. Deacylation of the galactopyranoside 10 under the same conditions also gave 11, due to base catalysed isomerisation of galacto to the more stable gluco configuration. The structure of 11, crystallized as the monohydrate, was confirmed by X-ray crystallographic analysis. The asymmetric unit contains two sugar molecules in two unique but similar conformations and two water molecules. The sulfo and the a
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- Author
- José G. Fernández-Bolaños; Salud Garcı́a; José Fernández-Bolaños; Ma Jesús Diánez; Ma Dolores Estrada; Amparo López-Castro; Simeón Pérez-Garrido
- Publisher
- Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0957-4166)
- Published
- 2003
- Language
- EN
- Field
- Chemistry (Physical Sciences)