The use of cesium dibenzyl and diphenyl phosphates for stereoselective synthesis of glycosyl phosphate derivatives |
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Authors: | P A Illarionov V I Torgov V N Shibaev |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation |
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Abstract: | Peracetates of β-glycosyl dibenzyl phosphates are formed efficiently in the reaction of cesium dibenzyl phosphate with peracetyl-α-glycosyl
nitrates derived froml-fucopyranose,d-galactopyranose, and 2-azido-2-deoxy-d-galactopyranose or with tri-O-acetyl-α-l-fucopyranosyl bromide. On the contrary, the reaction of the above-mentioned glycosyl nitrates with cesium diphenyl phosphate
leads to thermodynamically more stable α-glycosyl diphenyl phosphatevia intermediate formation of the corresponding β-anomers.
Published inIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 1924–1928, November, 2000. |
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Keywords: | glycosyl nitrates glycosyl phosphates phosphorylation stereospecificity |
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