263543-75-5

Upstream product

• 98-88-4 benzoyl chloride 
• 142924-31-0 S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 

Downstream Products

• 263543-69-7 ethyl 3-O-benzoyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-1-thia-α-D-mannopyranoside 
• 282088-48-6 ethyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-3-O-benzoyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 282088-50-0 ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-[2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)]-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 270917-79-8 ethyl 2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

Highly diastereoselective α-mannopyranosylation in the absence of participating protecting groups

S-Phenyl 2,6-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)- 1- thia-α-D-mannopyranoside and its sulfoxide, following activation at -78 °C with benzenesulfenyl triflate or trifiic anhydride, respectively, provide the corresponding α-mannosyl triflate as demonstrated by NMR spectroscopy. On addition of an acceptor alcohol α-mannosides are then formed. Similarly, S- phenyl 2,3-O-carbonyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside and ethyl 3-O-benzoyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-1-thia-α-D- mannopyranoside both provide α-mannosides on activation with benzenesulfenyl triflate followed by addition of an alcohol. These results stand in direct contrast to the highly β-selective couplings of comparable glycosylations with 2,3-di-O-benzyl-4,6-O-benzylidene protected mannosyl donors and draw attention to the subtle interplay of reactivity and structure in carbohydrate chemistry.

Synthesis of galactofuranosyl-containing oligosaccharides corresponding to the glycosylinositolphospholipid of Trypanosoma cruzi.

The oligosaccharide beta-D-Galf-(1-->3)-alpha-D-Manp-(1-->2)-[beta-D-Galf- (1-->3)]-alpha-D-Manp-(1-->2)-alpha-D-Manp corresponds to the terminal end of the glycosylinositolphospholipid oligosaccharide of the protozoan Trypanosoma cruzi, the causative agent of Chagas' disease. Syntheses of methyl or ethylthio glycosides of the terminal disaccharide, trisaccharide, tetrasaccharide, and pentasaccharide corresponding to this structure are described. These syntheses employ the selective activation of a phenyl 1-selenogalactofuranoside or a phenyl 1-selenomannopyranoside donor over ethyl 1-thioglycoside acceptors with NIS-TfOH.