Synthesis and study of the glycosyl-donor properties of 2-(2,2,2-trichloroethoxy)-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-d-galactopyrano)-[2,1-d]-2-oxazoline

Synthesis and study of the glycosyl-donor properties of 2-(2,2,2-trichloroethoxy)-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-d-galactopyrano)-[2,1-d]-2-oxazoline Full article

Journal

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

Output data

Year: 2024, Volume: 536, Article number : 109040, Pages count : DOI: 10.1016/j.carres.2024.109040

Authors

Pertel Sergey S. 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

A synthesis of 2-(2,2,2-trichloroethoxy)-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-d-galactopyrano)-[2,1-d]-2-oxazoline – a previously unknown 2-alkoxy glyco-[2,1-d]-2-oxazoline derivative with d-galacto configuration was carried out. Glycosylating activity of the obtained galactooxazoline has been studied and it has been shown that in the presence of a weak protic acid, such as sym-collidinium triflate, this substance exhibits properties of a reactive and 1,2-trans-stereoselective glycosyl donor. The homopolymerization reaction of oxazoline derivatives of sugars has been found to proceed under the same conditions, leading to the formation of pseudo-oligosaccharide products. It has been found that this undesirable side reaction could be suppressed by changing the acid catalyst concentration, resulting in the development of efficient methods for the synthesis of glycoside and oligosaccharide derivatives of β-d-galactosamine using the synthesized 2-(2,2,2-trichloroethoxy)-2-oxazoline glycosyl donor under very mild conditions.

Pertel S.S. , Kakayan E.S. , Zinin A.I. , Kononov L.O.
Synthesis and study of the glycosyl-donor properties of 2-(2,2,2-trichloroethoxy)-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-d-galactopyrano)-[2,1-d]-2-oxazoline
Carbohydrate Research. 2024. V.536. 109040 . DOI: 10.1016/j.carres.2024.109040 WOS Scopus OpenAlex

Web of science:	WOS:001164312200001
Scopus:	2-s2.0-85182624229
OpenAlex:	W4390705053

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