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Synthesis and conformations of 2,3:4,5- and 2,4:3,5-di-O-isopropylidene-d-mannitol

✍ Scribed by Krystyna Gawronska

Publisher: Elsevier Science
Year: 1988
Tongue: English
Weight: 413 KB
Volume: 176
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(88)84059-x

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✦ Synopsis

The 2,3:4,5-( 8) and 2,4:3,5-di-0-isopropylidene (10) derivatives of Dmannitol have been prepared from 1,6-di-0-benzoyl-D-mannitol and their structures established by 13C-n.m.r. spectroscopy. The 1,3-dioxane rings in 10 adopt a skew conformation and the sugar carbon chain in 8 is bent around the C-3-C-4 bond, as found by i.r. data and molecular mechanics calculations. Oxidation of 8 with pyridinium dichromate gave 2,3:4,5-di-0-isopropylidene-D-mannono-1,6lactone (12).

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