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 Full article

Journal

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

Output data

Year: 2003, Volume: 52, Number: 6, Pages: 1442-1446 Pages count : 5 DOI: 10.1023/a:1024855917480

Authors

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

Affiliations

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

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