Multigram scale synthesis of formyl tetra-O-benzyl-β-d-C-glucopyranoside using benzothiazole as a formyl group equivalent |
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Authors: | Alessandro Dondoni Alberto Marra |
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Institution: | Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, I-44100 Ferrara, Italy |
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Abstract: | The addition of 2-lithiobenzothiazole to d-gluconolactone followed by deoxygenation of the resulting ketose affords a mixture of benzothiazolyl α- and β-d-glucopyranoside; treatment of this mixture with sodium methoxide gives the β-anomer from which the title aldehyde is obtained in a pure form by transformation of the benzothiazole ring into the formyl group. |
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Keywords: | benzothiazole C-glycosides sugar aldehydes thiazole |
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