16697-40-8

Upstream product

• 86420-78-2 methyl 2,3-anhydro-4,6-O-benzylidene-β-D-talopyranoside 
• 3150-15-0 methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 
• 5188-07-8 sodium thiomethoxide 
• 129217-24-9 4,6-O-benzylidene-1-O-methyl-2-O-trifluoromethylsulfonate-α-D-glucopyranoside 

Downstream Products

• 56405-85-7 methyl-[O⁴,O⁶-((S)-benzylidene)-O²-methyl-β-D-lyxo-3-deoxy-hexopyranoside] 
• 14187-72-5 methyl-[O⁴,O⁶-((S)-benzylidene)-β-D-lyxo-3-deoxy-hexopyranoside] 
• 54898-13-4 methyl-[O²-ethoxycarbonyl-O⁴,O⁶-((S)-benzylidene)-S-methyl-3-thio-β-D-idopyranoside] 

Relevant academic research and scientific papers

Influence of steric bulk around the vinyl sulfone bond on the reaction patterns of vinyl sulfone-modified carbohydrates. An experimental and theoretical investigation

Steric bulks attached to sulfur atom of vinyl sulfone-modified hex-2-enopyranosides and the anomeric centre control the rate of reactions of these Michael acceptors. Amongst the two, the steric bulk at C-1 is more efficient in retarding the reaction rate of Michael addition reaction. The conformational analysis performed with 2a and 2e using quantum chemical calculations suggests that the addition of isopropyiamine would be slower for 2e compared to 2a due to the more steric hindrance in the former case.

Reactions of Some Pyranoside Diol Monotriflates with Nucleophiles and Bases

Reaction of pyranoside diol (equatorial) monotriflates with soft, nonbasic nucleophiles is a useful way to make axial heteroatom-substituted and "epimerized" pyranosides, particularly where a fused acetal ring inhibits ring contraction.Among the substrates examined (1,2,3,4,35), only 4 shows a strong tendency to give ring-contracted products.The reaction of 1-3 with more basic nucleophiles (F(1-), t-BuO(1-)) leads to the anhydrosugars 8, 25, and 26, respectively.The SN2 reaction of 35 with tetra n-butylammonium iodide forms the basis for a new synthesis of the Cerny epoxide 32.