New methods for the synthesis of 2-(2,2,2-trichloroethoxy)-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline and its use for stereo-, chemo- and regioselective glycosylation

New methods for the synthesis of 2-(2,2,2-trichloroethoxy)-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline and its use for stereo-, chemo- and regioselective glycosylation Full article

Journal

Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215

Output data

Year: 2022, Volume: 520, Article number : 108633, Pages count : DOI: 10.1016/j.carres.2022.108633

Authors

Pertel Sergey S ¹ , Seryi Sergey A ¹ , Kakayan Elena S ¹ , Zinin Alexander I ² , Kononov Leonid O ²

Affiliations

1	V.I. Vernadsky Crimean Federal University, Vernadsky Ave., 4, 295007, Simferopol, Russian Federation
2	N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp., 47, 119991, Moscow, Russian Federation

New methods for the synthesis of the title oxazoline 2 from the corresponding 2-deoxy-2-(2,2,2- trichloroethoxycarbonylamino)glucosyl bromide were developed. The target 2-(2,2,2-trichloroethoxy) gluco-[2,1-d]-2-oxazoline 2 can be synthesized under conditions of halide ion catalysis, using triethylamine as a base. The synthesized 2-(2,2,2-trichloroethoxy)-2-oxazoline glycosyl donor was used for stereo-, regio-, and chemoselective glycosylation reactions under extremely mild conditions. The undesirable side reaction of intermolecular aglycone transfer between an ethyl thioglycoside glycosyl acceptor and the 2-(2,2,2-trichloroethoxy)-2-oxazoline glycosyl donor occurred to a relatively small extent. Regio-, and chemoselectivity of the disaccharide synthesis with the oxazoline glycosyl donor depended on the reaction conditions.

Pertel S.S. , Seryi S.A. , Kakayan E.S. , Zinin A.I. , Kononov L.O.
New methods for the synthesis of 2-(2,2,2-trichloroethoxy)-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline and its use for stereo-, chemo- and regioselective glycosylation
Carbohydrate Research. 2022. V.520. 108633 . DOI: 10.1016/j.carres.2022.108633 WOS Scopus OpenAlex

Web of science:	WOS:000831538700005
Scopus:	2-s2.0-85134820271
OpenAlex:	W4285046085

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