65533-40-6

Upstream product

• 329307-82-6 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-trifyl-α-D-(2-2H)glucopyranoside 
• 329307-92-8 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-(2-2H)mannopyranoside 
• 329307-81-5 methyl 3-O-benzyl-4,6-O-benzylidene-α-D-(2-2H)glucopyranoside 
• 329307-84-8 methyl 3-O-benzyl-4,6-O-benzylidene-α-D-(2-2H)mannopyranoside 
• 90593-22-9 Methyl 3-O-benzyl-4,6-O-benzylidene-2-O-<(trifluoromethyl)sulfonyl>-α-D-glucopyranoside 
• 58381-45-6 methyl 3-O-benzyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose 
• 61893-77-4 methyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 23392-28-1 methyl 3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 2774-19-8 methyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 329307-71-3 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-trifyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

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.