187153-36-2

Upstream product

• 187152-77-8 ethyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 141810-60-8 ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 20701-61-5 ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 146608-95-9 ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 98-88-4 benzoyl chloride 
• 20701-61-5 ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 146530-63-4 ethyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 

Downstream Products

• 187153-41-9 ethyl 6-O-allyl-2-O-benzoyl-3,4-di-O-benzyl-1-thio-β-D-glucopyranoside 
• 1053628-36-6 Benzoic acid (2S,3R,4R,5R,6R)-4-benzyloxy-2-ethylsulfanyl-6-(2,2,2-trichloro-acetimidoyloxymethyl)-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester 
• 666753-81-7 Benzoic acid (4aS,6S,7R,8S,8aS)-8-benzyloxy-6-ethylsulfanyl-2-trichloromethyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-d][1,3]oxazin-7-yl ester 
• 187153-39-5 ethyl 6-O-allyl-2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranoside 
• 1053651-41-4 Benzoic acid (2S,3R,4S,5R,6R)-4-benzyloxy-2-ethylsulfanyl-5-hydroxy-6-(2,2,2-trichloro-acetimidoyloxymethyl)-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Automated access to well-defined ionic oligosaccharides

Ionic polysaccharides are part of many biological events, but lack structural characterisation due to challenging purifications and complex synthesis. Four monosaccharides bearing modifications not found in nature are used for the automated synthesis of a collection of ionic oligosaccharides. Structural analysis reveals how the charge pattern affects glycan conformation.

Synthesis of a pentasaccharide corresponding to the repeating unit of the exopolysaccharide from Cryptococcus neoformans serovar D

The assembly of the pentasaccharide repeating unit of the exopolysaccharide from Cryptococcus neoformans serovar D (i.e. 1) is described. The glucuronic acid residue in 1 is introduced as a glucopyranoside and oxidized in a later stage of the synthesis. Thus, iodonium ion-assisted glycosylation of the partially protected methyl mannopyranoside 11 with ethylthio donor 14 gave, after selective deprotection, disaccharide 18. Elongation of the latter with D-glucopyranoside 35 gave trisaccharide 36. Subsequent protective group manipulations yielded the acceptor 37. Condensation of disaccharide donor 31 with trisaccharide acceptor 37 yielded pentasaccharide 38. Protective group manipulations of 38 afforded 42, the glucoside of which was oxidized to yield the corresponding glucuronide 44. Hydrogenolysis of 44 gave the target pentasaccharide 1.