Glycosylation with derivatives of phenyl 2-azido-2-deoxy-1-seleno-α-d-gluco- and -α-d-mannopyranosides

Glycosylation with derivatives of phenyl 2-azido-2-deoxy-1-seleno-α-d-gluco- and -α-d-mannopyranosides Full article

Journal

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

Output data

Year: 2023, Volume: 72, Number: 3, Pages: 785-792 Pages count : 8 DOI: 10.1007/s11172-023-3842-6

Authors

Tokatly A.I. ¹ , Vinnitsky D.Z. ¹ , Kamneva A.A. ¹ , Yashunsky D.V. ¹ , Tsvetkov Y.E. ¹ , Nifantiev N.E. ¹

Affiliations

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

Glycosylation of primary (3-trifluoroacetamidopropanol) and secondary (methyl 2,3-O-isopropylidene-α-L-rhamnopyranoside) alcohols with phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-D-glucopyranoside in the presence of N-iodosuccinimide and trimethylsilyl triflate in diethyl ether afforded the corresponding 2-azido-2-deoxyglu-cosides in rather high yields and with good α-stereoselectivity (α:β = 3−5:1). Similar glycosylation with phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-D-manno-pyranoside resulted exclusively in α-linked 2-azido-2-deoxymannosides.

Tokatly A.I. , Vinnitsky D.Z. , Kamneva A.A. , Yashunsky D.V. , Tsvetkov Y.E. , Nifantiev N.E.
Glycosylation with derivatives of phenyl 2-azido-2-deoxy-1-seleno-α-d-gluco- and -α-d-mannopyranosides
Russian Chemical Bulletin. 2023. V.72. N3. P.785-792. DOI: 10.1007/s11172-023-3842-6 WOS Scopus OpenAlex

≡ Web of science:	WOS:001031662300020
≡ Scopus:	2-s2.0-85153285795
≡ OpenAlex:	W4365816089