The effect of high pressure on the stereospecificity of the glycosylation reaction

At a pressure of 1.4 GPa and room temperature, the glycosylation of trityl ethers by 1,2- O-cyanoethylidene derivatives of sugars, and the polycondensation of the proper monomers in dichloromethane, proceed with absolute stereospecificity, giving rise to a 1,2- trans-glycosidic linkage, although, at...

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Bibliographic Details
Published in:Carbohydrate research 1987-07, Vol.164, p.241-254
Main Authors: Kochetkov, Nikolay K., Zhulin, Victor M., Klimov, Evgeny M., Malysheva, Nelly N., Makarova, Zinaida G., Ott, Andrej Ya
Format: Article
Language:English
Subjects:
Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
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Summary:At a pressure of 1.4 GPa and room temperature, the glycosylation of trityl ethers by 1,2- O-cyanoethylidene derivatives of sugars, and the polycondensation of the proper monomers in dichloromethane, proceed with absolute stereospecificity, giving rise to a 1,2- trans-glycosidic linkage, although, at the ambient pressure, the reactions studied reveal a rather low stereospecificity. The effect of high pressure on the stereospecificity of glycosidic linkage formation is explained as being due to the shift of the equilibrium between monocyclic glycosyl-cation and bicyclic acyloxonium cation towards the latter as the pressure is increased.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(87)80133-7