Synthesis of a cyclic tetramer of 3-amino-3-deoxyallose with axially oriented amino groups

Synthesis of a cyclic tetramer of 3-amino-3-deoxyallose with axially oriented amino groups Full article

Journal

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

Output data

Year: 2022, Volume: 511, Article number : 108476, Pages count : DOI: 10.1016/j.carres.2021.108476

Authors

Yudina Olga N. ¹ , Gening Marina L. ¹ , Talukdar Pinaki ² , Gerbst Alexey G. ¹ , Tsvetkov Yury E. ¹ , Nifantiev Nikolay E. ¹

Affiliations

1	Laboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp, 119991, Moscow, Russian Federation.
2	Department of Chemistry, Indian Institute of Science Education and Research Pune, Dr. Homi Bhabha Road, Pashan, Pune, 411008, Maharashtra, India

A linear tetramer of β-(1 → 6)-linked 3-azido-3-deoxy-d-allose containing glycosyl donor and glycosyl acceptor functions in the terminal monosaccharide units was prepared starting from 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-d-allofuranose. Cyclization of the linear tetramer under glycosylation conditions afforded the corresponding cyclic tetrasaccharide in 77% yield; its deprotection and reduction of the azido groups resulted in the formation of the cyclic tetramer of 3-amino-3-deoxy-d-allose with axial amino groups, a potential scaffold for the synthesis of tetravalent functional clusters.

Yudina O.N. , Gening M.L. , Talukdar P. , Gerbst A.G. , Tsvetkov Y.E. , Nifantiev N.E.
Synthesis of a cyclic tetramer of 3-amino-3-deoxyallose with axially oriented amino groups
Carbohydrate Research. 2022. V.511. 108476 . DOI: 10.1016/j.carres.2021.108476 WOS Scopus OpenAlex

≡ Web of science:	WOS:000720842500002
≡ Scopus:	2-s2.0-85119294635
≡ OpenAlex:	W3211432221