Efficient regeneration of the 5-acetamido group of a neuraminic acid aryl glycoside from the O-nethyl acetimidate function under acidic conditions

Efficient regeneration of the 5-acetamido group of a neuraminic acid aryl glycoside from the O-nethyl acetimidate function under acidic conditions Full article

Journal

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

Output data

Year: 2009, Volume: 58, Number: 2, Pages: 442-445 Pages count : 4 DOI: 10.1007/s11172-010-0030-6

Authors

Orlova A.V. ¹ , Zinin A.I. ¹ , Kononov L.O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

Treatment of protected N-acetylneuraminic acid 2-formyl-4-nitrophenyl glycoside with (diethyl-amino)sulfur trifluoride (DAST) and methanol resulted, apart from the known transformation of the formyl group into a difluoromethyl one, in an undocumented formation of 5-(O-methyl acetimidate) of Neu5Ac. This imidate was converted into the target 5-acetamido derivative under the action of aqueous TFA. The yield of the target product (94%) was twice as high as that reported earlier.

Orlova A.V. , Zinin A.I. , Kononov L.O.
Efficient regeneration of the 5-acetamido group of a neuraminic acid aryl glycoside from the O-nethyl acetimidate function under acidic conditions
Russian Chemical Bulletin. 2009. V.58. N2. P.442-445. DOI: 10.1007/s11172-010-0030-6 WOS Scopus OpenAlex

Web of science:	WOS:000275907000026
Scopus:	2-s2.0-77950229850
OpenAlex:	W1968770648

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