The formation of isopropylidene acetals of erythritol and ribitol under conditions of kinetic control

The isopropylidenation of erythritol, under conditions of kinetic control, employing 2-methoxypropene, yielded the 1,2:3,4- ( 1, 50%), the 1,4:2,3- ( 2, 18%), and the novel 1,3:2,4-diacetal ( 3, 5%). Under similar conditions, ribitol gave the known 1,2:4,5- ( 4, 36%) and 1,4:2,3-diacetal ( 7, 3%) to...

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Bibliographic Details
Published in:Carbohydrate research 1990-09, Vol.205, p.173-179
Main Authors: Awal, Abdul, Boyd, Alan S.F., Grant Buchanan, J., Edgar, Alan R.
Format: Article
Language:English
Subjects:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary:The isopropylidenation of erythritol, under conditions of kinetic control, employing 2-methoxypropene, yielded the 1,2:3,4- ( 1, 50%), the 1,4:2,3- ( 2, 18%), and the novel 1,3:2,4-diacetal ( 3, 5%). Under similar conditions, ribitol gave the known 1,2:4,5- ( 4, 36%) and 1,4:2,3-diacetal ( 7, 3%) together with the new 1,3:4,5- ( 8, 12%) and 1,3:2,5- diacetal ( 11, 5%), a further example of a dioxepane ring. 13C-N.m.r. and 1H-n.m.r. spectroscopy showed that the 1,3-dioxane rings in 3, 8, and 11 adopt chair conformations. In 9, the p-nitrobenzoate of 8, the dioxane chair is flattened. The product composition is compared with that from the equilibrated system.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(90)80137-R