Synthesis of derivatives of 2-amino-2-deoxy-4-O-(α- and β-d-galactopyranosyl)-d-glucose

Synthesis of derivatives of 2-amino-2-deoxy-4-O-(α- and β-d-galactopyranosyl)-d-glucose Full article

Journal

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

Output data

Year: 1988, Volume: 174, Pages: 61-72 Pages count : 12 DOI: 10.1016/0008-6215(88)85081-x

Authors

Nifant'ev Nikolay E. ¹ , Backinowsky Leon V. ¹ , Kochetkov Nikolay K. ¹

Affiliations

1	N.D. Zelinksy Institute of Organic Chemistry, Academy of Sciences of the U.S.S.R., Moscow U.S.S.R.

Galactosylation of methyl 6-O-acetyl-3-O-benzoyl-2-deoxy-2-phthalimido-β-d-glucopyranoside (5) and its trityl ether 9 with 2,3,4,6-tetra-O-benzoyl-α-d-galactopyranosyl bromide (8), 1-O-acetyl-2,3,4,6-tetra-O-benzoyl-β-d-galactopyranose (13), 3,4,6-tri-O-benzoyl-1,2-O-(α-p-tolythiobenzylidene)-α-d-galactopyranose (11), and 3,4,6-tri-O-benzoyl-1,2-O-(α-cyanobenzylidene)-α-d-galactopyranose (12) gave 1,2-cis- and 1,2-trans-linked disaccharide derivatives in ratios ranging from 3.8:1 to 1:8.5 depending on the conditions of glycosylation. A practical synthesis of the target lactosamine derivative 2 was achieved by the reaction of 5 and 8 in nitromethane in the presence of silver triflate.

Nifant'ev N.E. , Backinowsky L.V. , Kochetkov N.K.
Synthesis of derivatives of 2-amino-2-deoxy-4-O-(α- and β-d-galactopyranosyl)-d-glucose
Carbohydrate Research. 1988. V.174. P.61-72. DOI: 10.1016/0008-6215(88)85081-x WOS Scopus OpenAlex

≡ Web of science:	WOS:A1988M732700007
≡ Scopus:	2-s2.0-0007194992
≡ OpenAlex:	W2053807018