369386-67-4

Upstream product

• 108-24-7 acetic anhydride 
• 188472-80-2 ethyl 2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 
• 573699-48-6 ethyl 2,6-di-O-benzyl-3,4-O-endo-benzylidene-1-thio-β-D-galactopyranoside 
• 213459-71-3 ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 215371-44-1 ethyl 2,6-di-O-benzyl-1-thio-β-D-galactopyranoside 

Downstream Products

• 419549-59-0 Acetic acid (3R,4S,5S,6R)-2-(5-azido-pentyloxy)-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester 
• 419549-76-1 5-azidopentyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 419549-77-2 5-azidopentyl (3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 419549-70-5 5-azidopentyl (4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 419549-71-6 5-azidopentyl (3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 419549-61-4 5-azidopentyl 2,4,6-tri-O-benzyl-α-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis of Aminoethyl Glycosides of the Carbohydrate Chains of Glycolipids Gb3, Gb4, and Gb5

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.

Synthesis of fragments of the glycocalyx glycan of the parasite Schistosoma mansoni

The chemical synthesis of α-L-Fucp-(1→3)-β-D-GalpNAc-(1→4)-β-D-GlcpNAc- (1→3)-α-D-GalpO(CH2)5NH2, β-D-GalpNAc-(1→4)-[α-L-Fucp-(1→3)-]β-D-GlcpNAc- (1→3)-α-D-GalpO(CH2)5NH2, and α-L-Fucp-(1→3

Synthesis of oligosaccharides corresponding to Streptococcus pneumoniae type 9 capsular polysaccharide structures

Two trisaccharides, α-D-Galp-(1→3)-β-D-ManpNAc-(1→4)-β-D-Glcp and α-D-Glcp-(1→3)-β-D-ManpNAc-(1→4)-β-D-Glcp, corresponding to structures from Streptococcus pneumoniae capsular polysaccharides type 9A, L, V and type 9N, respectively, have been synthesised