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. © 2002 Elsevier Science Ltd. All rights reserved.
Multigram scale synthesis of formyl tetra-O-benzyl-beta-D-C-glucopyranoside using benzothiazole as a formyl group equivalent
DONDONI, Alessandro;MARRA, Alberto
2003
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. © 2002 Elsevier Science Ltd. All rights reserved.File in questo prodotto:
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