Selective preparation of glycosyl sulfone or glycal by treatment of phenyl thioglycoside of N-acetylneuraminic acid with m-chloroperbenzoic acid Научная публикация
| Журнал |
Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285 |
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| Вых. Данные | Год: 2002, Том: 51, Номер: 4, Страницы: 698-702 Страниц : 5 DOI: 10.1023/a:1015884605482 | ||
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Реферат:
Treatment of acetylated phenyl thioglycoside of N-acetylneuraminic acid with m-chloroperbenzoic acid (MCPBA) in CH2Cl2 affords quantitatively mixtures of the respective sulfone and glycal free from the sulfoxide. The outcome of the reaction does not depend on the anomeric configuration of the starting thioglycoside. The sulfone can be selectively prepared (yield ∼100%) by oxidation with an excess of MCPBA and NaHCO3. In the presence of pyridine (2 equiv.) and MCPBA (2 equiv.), the major product is glycal (yields 81—88%). This version of the reaction can be regarded as a new method for the preparation of sialic acid glycals.
Библиографическая ссылка:
Kononov L.O.
, Komarova B.S.
, Nifantiev N.E.
Selective preparation of glycosyl sulfone or glycal by treatment of phenyl thioglycoside of N-acetylneuraminic acid with m-chloroperbenzoic acid
Russian Chemical Bulletin. 2002. V.51. N4. P.698-702. DOI: 10.1023/a:1015884605482 WOS Scopus OpenAlex
Selective preparation of glycosyl sulfone or glycal by treatment of phenyl thioglycoside of N-acetylneuraminic acid with m-chloroperbenzoic acid
Russian Chemical Bulletin. 2002. V.51. N4. P.698-702. DOI: 10.1023/a:1015884605482 WOS Scopus OpenAlex
Идентификаторы БД:
| Web of science: | WOS:000176530300022 |
| Scopus: | 2-s2.0-0141498091 |
| OpenAlex: | W2953389305 |