Approaches to intramolecular sialylation. 2. Synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid containing an unprotected carboxy group

Approaches to intramolecular sialylation. 2. Synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid containing an unprotected carboxy group Научная публикация

Журнал

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Вых. Данные

Год: 2003, Том: 52, Номер: 6, Страницы: 1442-1446 Страниц : 5 DOI: 10.1023/a:1024855917480

Авторы

Kononov L.O. ¹ , Shpirt A.M. ² , Ito Y. ³ , Ogawa T. ³

Организации

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow (Russian Federation)
2	Higher Chemical College of the Russian Academy of Sciences, Moscow, Russian Federation
3	Institute of Physical and Chemical Research (RIKEN), Wako-shi, Saitama, Japan

Various approaches to the synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid (Neu5Ac) containing an unprotected carboxy group starting from the corresponding methyl esters were comparatively studied. One-step demethylation of methyl thioglycoside (LiI, Py, reflux) proceeded inefficiently in contrast to the analogous smooth reaction of phenyl thioglycoside. An indirect route to derivatives with a free carboxy group involving saponification followed by acetylation of hydroxy groups proved to be more efficient for methyl α-thioglycoside of Neu5Ac.

Kononov L.O. , Shpirt A.M. , Ito Y. , Ogawa T.
Approaches to intramolecular sialylation. 2. Synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid containing an unprotected carboxy group
Russian Chemical Bulletin. 2003. V.52. N6. P.1442-1446. DOI: 10.1023/a:1024855917480 WOS Scopus OpenAlex

Web of science:	WOS:000185213100030
Scopus:	2-s2.0-1642573245
OpenAlex:	W2953270179

БД	Цитирований
OpenAlex	4
Scopus	2
Web of science	2