183875-28-7

Upstream product

• 68779-52-2 1,2-O-(1-methoxyethylidene)-3,4,6-tri-O-benzyl-α-D-galactopyranose 
• 108-98-5 thiophenol 
• 4551-15-9 phenylthiotrimethylsilane 
• 77790-46-6 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranose 

Downstream Products

• 183875-13-0 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-((2R,4aR,6R,7R,8R,8aS)-7-azido-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 183875-14-1 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-azido-4-((2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester 
• 183875-31-2 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-((2R,3R,4R,5S,6R)-3-azido-5-hydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 183875-32-3 C₃₉H₄₃N₃O₉S 
• 183875-30-1 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 213185-39-8 phenyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside 
• 204199-48-4 phenyl (3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-[4,6-di-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside 
• 213185-40-1 phenyl [3,4,6-tri-O-benzyl-α-D-galactopyranosyl]-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside 
• 213185-35-4 phenyl 3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside 
• 213185-38-7 phenyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1->3)-(4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside 
• 204199-47-3 phenyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1->3)-(4,6-di-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside 
• 259871-02-8 phenyl 3,4,6-tri-O-benzyl-2-O-(2-O-benzoyl-1,4-di-O-benzyl-α-D-glucopyranos-3-yloxycarbonylpropanoyl)-1-thio-β-D-galactopyranoside 
• 259871-01-7 phenyl 3,4,6-tri-O-benzyl-2-O-(2-O-benzoyl-1-O-benzyl-4,6-O-benzylidene-α-D-glucopyranos-3-yloxycarbonylpropanoyl)-1-thio-β-D-galactopyranoside 
• 259871-07-3 benzyl O-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-2',3'-succinate 

Relevant academic research and scientific papers

Prearranged glycosides. Part 8. Intramolecular α-galactosylation via succinoyl tethered glycosides

Benzyl protected phenyl 1-thio-galactopyranoside donors which were tethered by a succinoyl linker at their positions 2 and 6, respectively, to position 3 of a blocked benzyl glucopyranoside acceptor with a 4-OH group solely afforded the corresponding α-(1→4)-linked disaccharides upon intramolecular glycosylation. 4,6-Siloxane protected mannosides react with rearrangement of the siloxane group under similar conditions.

Synthesis of glycoconjugate vaccines against Shigella dysenteriae type 1

Syntheses of hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglycon-linked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.