Convenient Synthesis and Purification ofN-Trifluoroacetylated Neuraminic Acid Tetraol: A Key Precursor for the Synthesis of New Sialyl Donors Containing LabileO-Acyl Protecting Groups

Convenient Synthesis and Purification ofN-Trifluoroacetylated Neuraminic Acid Tetraol: A Key Precursor for the Synthesis of New Sialyl Donors Containing LabileO-Acyl Protecting Groups Full article

Journal

Journal of Carbohydrate Chemistry
ISSN: 0732-8303 , E-ISSN: 1532-2327

Output data

Year: 2014, Volume: 33, Number: 5, Pages: 213-224 Pages count : 12 DOI: 10.1080/07328303.2014.913058

Authors

Podvalnyy Nikita M. ¹ , Zinin Alexander I. ¹ , Malysheva Nelly N. ¹ , Kunetskiy Roman A. ¹ , Kononov Leonid O. ¹

Affiliations

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

A convenient synthesis and separation of α- and β-anomers of methyl (phenyl 3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-D-galacto-nonulopyranosid)onate (6a and 6b) on a multigram scale was developed. Both α- and β-isomers of 6 were obtained as crystals suitable for safe storage. The β-isomer forms a crystalline solvate with methanol. Fully O-trichloroacetylated and O-trifluoroacetylated N-trifluoroacetyl thiosialosides were synthesized in an efficient manner from the β-tetraol 6b.

Podvalnyy N.M. , Zinin A.I. , Malysheva N.N. , Kunetskiy R.A. , Kononov L.O.
Convenient Synthesis and Purification ofN-Trifluoroacetylated Neuraminic Acid Tetraol: A Key Precursor for the Synthesis of New Sialyl Donors Containing LabileO-Acyl Protecting Groups
Journal of Carbohydrate Chemistry. 2014. V.33. N5. P.213-224. DOI: 10.1080/07328303.2014.913058 WOS Scopus OpenAlex

Web of science:	WOS:000337946800001
Scopus:	2-s2.0-84903588160
OpenAlex:	W2003980018

DB	Citing
OpenAlex	5
Scopus	5
Web of science	6