65925-95-3

Upstream product

• 129706-93-0 methyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 95587-91-0 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(trifluoromethanesulfonyl)-β-D-glucopyranoside 
• 14155-23-8 methyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 67-68-5 dimethyl sulfoxide 
• 709-50-2 methyl beta-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 329307-87-1 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-trifyl-β-D-(2-2H)mannopyranoside 
• 129706-93-0 methyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 2774-19-8 methyl 3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside 
• 329307-86-0 methyl 3-O-benzyl-4,6-O-benzylidene-β-D-(2-2H)mannopyranoside 
• 23392-28-1 methyl 3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 142644-82-4 methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-methylene-β-D-arabino-hexopyranosid 

Relevant academic research and scientific papers

Synthesis of novel HIV-1 protease inhibitors based on carbohydrate scaffolds

The synthesis of peptidomimetic inhibitors of HIV-1 protease based on 6-deoxy-6-amino-β-D-glucopyranoside and 6-deoxy-6-amino-β-D-mannopyranoside scaffolds has been achieved. The inhibitors had IC50 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.

Reactions of some 2- and 4-O-triflylglycopyranosides with MeLi, t-BuOK, and pyridine

As an extension of our previous work on secondary triflates of carbohydrates [El Nemr, A.; Tsuchiya, T. Tetrahedron Lett. 1995, 36, 7665-7668. El Nemr, A.; Tsuchiya, T.; Kobayashi, Y. Carbohydr. Res. 1996, 293, 31-59. El Nemr, A.; Tsuchiya, T. Carbohydr. Res. 1997, 301, 77-87. El Nemr, A.; Tsuchiya, T. Carbohydr. Res. 1997, 303, 267-281], the reaction modes of several methyl 2- and 4-O-triflyl-D-glycopyranosides with MeLi (strong base), t-BuOK (moderately strong base), and pyridine (weak base) have been studied. This paper describes the reactions of 3-O-benzyl-4,6-O-benzylidene-2-O-triflyl-D-gluco and -mannopyranosides with MeLi to give mainly the corresponding 2-C-methyl derivatives through α-elimination, with t-BuOK to give either the 2,3-unsaturated compounds through β-elimination or detriflyl 2-ols, and with hot pyridine to give the corresponding 2-pyridinium salts with inversion (except for the 2-O-triflyl-α-D-mannopyranoside (8)). 2,3,6-Tri-O-benzyl-4-O-triflyl-α-D-gluco and -mannopyranosides were also examined similarly.

Synthesis of the immunodominant trisaccharide related to the antigen from E. coli O126

The trisaccharide derivative methyl 2-O-[4,6-di-O-acetyl-3-O-(2,3,4,6)-tetra-O-benzyl-α-D-gal-actopyranos yl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-4,6-O-benzylidene-β-D- mannopyranoside (12) was obtained when 3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopy