663608-36-4Relevant academic research and scientific papers
Synthesis of Aminoethyl Glycosides of the Carbohydrate Chains of Glycolipids Gb3, Gb4, and Gb5
Cheshev,Khatuntseva,Gerbst,Tsvetkov,Shashkov,Nifantiev
, p. 372 - 381 (2007/10/03)
4-O-Glycosylation of 2-azidoethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,6-tri-O- benzoyl-β-D-galactopyranosyl)-β-D-glucopyranoside with ethyl 2,3,4,6-tetra-O-benzyl- and ethyl 3-O-acetyl-2,4,6-tri-O-benzyl-1-thio-α- D-galactopyranoside in the presence of methyl trifluoromethanesulfonate led to trisaccharide 2-azido-ethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)- (1→4)-(2,3,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3, 6-tri-O-benzoyl-β-D-glucopyranoside and its 3″-O-acetylated analogue, 2-azidoethyl (3-O-acetyl-2,4,6-tri-O-benzyl-α-D-galactopyranosyl)- (1→4)-(2,3,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3, 6-tri-O-benzoyl-β-D-glucopyranoside in yields of 85 and 83%, respectively. Deacetylation of the latter compound and subsequent glycosylation with 4-trichloroacetamidophenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloro- acetamido-β-D-galactopyranoside and 4-trichloroacetamidophenyl 4,6-di-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) -1-thio-2-trichloroacetamido-β-D-galactopyranoside in dichloromethane in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid resulted in the corresponding selectively protected derivatives of the tetrasaccharide GalNAc(β1→3)Gal(α1→4)Gal(β1→4)Glcβ-OCH 2CH2N3 and the pentasaccharide Gal(β1→3)GalNAc(β1→3)Gal(α→4)Gal(β1→4) Glcβ-OCH2CH2N3 in 88 and 73% yields, respectively. Removal of O-protecting groups, substitution of acetyl group for the N-trichloroacetyl group, and reduction of the aglycone azide group resulted in the target 2-aminoethyl globo-tri-, -tetra-, and -pentasaccharide, respectively.
