Some 3,5-acetal derivatives of d-glucitol

✍ Scribed by A. Jabbar Al-Kadir; Neil Baggett; John M. Webber

• Book ID: 102998662
• Publisher: Elsevier Science
• Year: 1992
• Tongue: English
• Weight: 592 KB
• Volume: 232
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(92)80058-9

✦ Synopsis

Ethylidenation of 1,6-di-O-benzoyl-2,4-0-benzylidene-o-glucitol gave the 3,5-0-ethylidene derivative in poor yield, whereas reaction with 2,2_dimethoxypropane gave the 3,5-0-isopropylidene derivative in good yield. Removal of the benzoyl and benzylidene groups, with further derivatisation, gave a variety of compounds containing the relatively unstable 3,5-acetal ring. Attempted tosylation of 3,5-O-isopropylidene-o-glucitol gave a derivative of 1,4-anhydro-o-glucitol. Reduction of various ditosylates revealed selective reaction of axial tosyloxymethyl groups.