68044-34-8

Upstream product

• 15038-71-8 methyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 108739-90-8 methyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 71117-36-7 methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 
• 86420-73-7 methyl 3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 108739-91-9 methyl 4,6-O-benzylidene-β-D-galactopyranoside 2-O-benzoate 

Downstream Products

• 192636-86-5 methyl 2-O-benzyl-4,6-O-benzylidene-β-D-(3-2H)glucopyranoside 
• 198020-87-0 methyl 2-O-benzyl-4,6-O-benzylidene-β-D-(3-2H)allopyranoside 
• 198020-80-3 C₂₂H₂₂⁽²⁾HF₃O₈S 
• 198020-88-1 methyl 2-O-benzyl-4,6-O-benzylidene-3-O-triflyl-β-D-(3-2H)allopyranoside 
• 108739-97-5 methyl 2-O-benzyl-4,6-O-benzylidene-3-C-methylene-β-D-xylo-hexopyranoside 
• 108672-12-4 methyl 2,6-di-O-benzyl-3-deoxy-3-C-methyl-β-D-galactopyranoside 
• 108739-98-6 methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-β-D-galactopyranoside 
• 108671-67-6 methyl 2,6-di-O-benzyl-3-deoxy-3-C-methyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside 

Relevant academic research and scientific papers

α- And β-hydrogen eliminations in the reactions of some 3-O-triflylglycosides with (t)BuOK and pyridine

Previous papers [10-12] reported new reactions that occur when some carbohydrate triflates are treated with MeLi (or BuLi) in Et2O to give the C-methyl(butyl) or unsaturated compounds through elimination of the CH-hydrogen bearing a CF3SO3 group ( α-elimination) as a proton. This paper extends the previous work and describes the reactions for some 3-O-triflyl-D-gluco- and -allo-furanosides and -pyranosides with (t)BuOK and pyridine [instead of Me(Bu)Li], utilizing the corresponding 2- and 3-deuterated analogs. It was found that, when (t)BuOK was used, the 3-O-triflyl-D-glucopyranosides gave 2,3- and 3,4-unsaturated compounds through a-hydrogen elimination (a-elimination) followed by (possibly) C-3 carbene formation, while the 3-O-triflyl-D-allopyranosides gave mainly 2,3-unsaturated compounds through p-elimination. When pyridine was used, most of the compounds gave the corresponding 3-pyridinium derivatives through an SN2 process.

SYNTHETIC RECEPTOR ANALOGUES: PREPARATION OF THE 3-O-METHYL, 3-C-METHYL, AND 3-DEOXY DERIVATIVES OF METHYL 4-O-α-D-GALACTOPYRANOSYL-β-D-GALACTOPYRANOSIDE (METHYL β-D-GALABIOSIDE)

Methyl β-D-galactopyranoside was transformed into methyl 2-O-benzyl- (5, 24percent) and 2-O-benzyloxymethyl-4,6-O-benzylidene-β-D-galactopyranoside (8, 60percent) in two and four steps respectively.Compounds 5 and 8 were then transformed into the correspo