Multigram scale synthesis of formyl tetra-O-benzyl-β-d-C-glucopyranoside using benzothiazole as a formyl group equivalent

✍ Scribed by Alessandro Dondoni; Alberto Marra

• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 211 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02525-x

✦ Synopsis

The addition of 2-lithiobenzothiazole to D-gluconolactone followed by deoxygenation of the resulting ketose affords a mixture of benzothiazolyl aand b-D-glucopyranoside; treatment of this mixture with sodium methoxide gives the b-anomer from which the title aldehyde is obtained in a pure form by transformation of the benzothiazole ring into the formyl group.