129706-94-1

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 40010-11-5 methyl β-D-glucopyranoside 3-benzyl ether 
• 129706-93-0 methyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 71117-37-8 (2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 709-50-2 methyl beta-D-glucopyranoside 

Downstream Products

• 1313873-68-5 methyl 3-O-benzyl-4,6-O-benzylidene-2C-methylene-β-D-arabino-hexopyranoside 
• 1313873-75-4 (1R,3R,4R,5S,6S)-3-methoxy-2-oxabicyclo[2.2.2]octane-4,5,6-triol 
• 1313873-74-3 (1R,3R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-methoxy-2-oxabicyclo[2.2.2]oct-7-ene 
• 1313873-73-2 methyl 2,3,4-tri-O-benzyl-2,5-di-C-vinyl-β-D-xylopyranoside 
• 1313873-72-1 methyl 2,3,4-tri-O-benzyl-2-C-vinyl-β-D-glucopyranoside 
• 1313873-71-0 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-2-C-vinyl-β-D-glucopyranoside 
• 1313873-70-9 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-2C-hydroxymethyl-β-D-glucopyranoside 
• 1313873-69-6 methyl 3-O-benzyl-4,6-O-benzylidene-2C-hydroxymethyl-β-D-glucopyranoside 
• 146668-91-9 N-((2R,4aR,6R,7S,8R,8aS)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ylmethyl)-acetamide 
• 146668-90-8 Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-nitromethyl-β-D-mannopyranoside 
• 156917-50-9 methyl 4-O-acetyl-3,6-di-O-benzyl-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-mannopyranoside 
• 156917-49-6 methyl 3,6-di-O-benzyl-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-mannopyranoside 
• 86363-44-2 methyl 3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside 
• 134131-55-8 methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2,2-difluoro-β-D-arabino-hexopyranoside 

Relevant academic research and scientific papers

Direct experimental evidence for the high chemical reactivity of α- and β-xylopyranosides adopting a 2,5B conformation in glycosyl transfer

The effect of a 2,5B boat conformation on xyloside reactivity has been investigated by studying the hydrolysis and glycosylation of a series of synthetic xyloside analogues based on a 2-oxabicyclo[2.2.2]octane framework, which forces the xylose analogue to adopt a 2,5B conformation. The locked β-xylosides were found to hydrolyze 100-1200 times faster than methyl β-D-xylopyranoside, whereas the locked α-xylosides hydrolyzed up to 2× 104 times faster than methyl α-D-xylopyranoside. A significant rate enhancement was also observed for the glycosylation reaction. The high reactivity of these conformers can be related to the imposition of a 2,5B conformation, which approximates a transition state (TS) boat conformation. In this way, the energy penalty required to go from the chair to the TS conformation is already paid. These results parallel and support the observation that the GH-11 xylanase family force their substrate to adopt a 2,5B conformation to achieve highly efficient enzymatic glycosidic bond hydrolysis. Copyright

Structure-based design and synthesis of HIV-1 protease inhibitors employing beta-D-mannopyranoside scaffolds.

A preliminary account on the structure-based design, synthesis and evaluation of peptidomimetic inhibitors of HIV-1 protease containing beta-D-mannopyranoside scaffolds is given. The compounds prepared had IC(50) values in the micromolar range. The results provide a platform for the development of more potent carbohydrate-based inhibitors of HIV-1 and other aspartic proteases.

Synthesis of three tetrasaccharides containing 3-O-methyl-D-mannose, as model compounds for xylose-containing carbohydrate chains from N-glycoproteins

The synthesis is reported of methyl 3,6-di-O-(3-O-methyl-α-D-mannopyranosyl)-2-O-β-D-xylopyranosyl-β-D-mannopyranoside (2), methyl 6-O-α-D-mannopyranosyl-3-O-(3-O-methyl-α-D-mannopyranosyl)-2-O-β-D-xylopyranosyl-β-D-mannopyranoside (3), and methyl 3-O-α-D-mannopyranosyl-6-O-(3-O-methyl-α-D-mannopyranosyl)-2-O-β-D-xylopyranosyl-β-D-mannopyranoside (4).The various methyl β-D-Man p acceptor derivatives were prepared from the corresponding methyl β-D-Glc p derivatives via oxidation-reduction.All glycosyl donors were coupled using the trichloroacetimidate method at -40 degC in dichloromethane with trimethylsilyl triflate as a catalyst.Methyl-3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside (7) was condensed with 2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate (8).Regioselective reductive 4,6-O-benzylidene ring-opening on the resulting disaccharide derivative, followed by acetylation, and hydrogenation gave methyl 4-O-acetyl-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-mannopyranoside (12).Coupling of 12 with 2,4,6-tri-O-acetyl-3-O-methyl-α-D-mannopyranosyl trichloroacetimidate (18) afforded tetrasaccharide derivative 19, and subsequent O-deacetylation gave 2.Methyl 3-O-benzyl-4,6-O-prop-2-enylidene-β-D-mannopyranoside (22) was condensed with 2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate (8).Regioselective reductive 4,6-O-prop-2-enylidene ring-opening on the resulting disaccharide derivative, followed by acetylation, and deallylation at O-6 gave methyl 4-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-mannopyranoside (26-a), which was either condensed with 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroacetimidate (27) or 18, to give trisaccharide derivatives 28 or 31, respectively.Debenzylation of 28 followed by condensation with 18 gave, after O-deacetylation, 3, whereas debenzylation of 31 followed by condensation with 27 gave, after O-deacetylation, 4.