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Formation, and stereochemistry, of 1,2-O-(1-methyl-1,2-ethanediyl)-d-glucose acetals formed in the acid-catalyzed hydrolysis of O-(2-hydroxypropyl)cellulose

✍ Scribed by Dae-Sil Lee; Arthur S. Perlin

Publisher: Elsevier Science
Year: 1984
Tongue: English
Weight: 883 KB
Volume: 126
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(84)85129-0

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✦ Synopsis

In the hydrolysis of O-(2-hydroxypropyl)cellulose, residues of D-gh.ICOSe substituted with a single O-(2-hydroxypropyl) substituent at O-2 (irrespective of the pattern of additional substitution at O-3 or O-6) form 1,2-0-(1-methyl-1,2ethanediyl)-a-D-glucose acetals. Based on the characteristics of 2-0-(2-hydroxypropyl)-D-glucose and derivatives thereof in aqueous acid, these bicyclic products are shown to comprise a mixture of two furanose and two pyranose species that differ widely in relative stability, depending on the chirality of C-8 of the 1,4-dioxane ring of the compounds.

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