1020653-97-7

Upstream product

• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 1826-67-1 vinyl magnesium bromide 

Downstream Products

• 1020654-01-6 (2,3,6-tri-O-benzyl-β-D-galactofuranosyl)ethene 
• 1138154-38-7 (2,3,5,6-tetra-O-benzyl-β-D-galactofuranosyl)ethene 
• 1020653-99-9 C₄₀H₄₄O₈ 
• 1448614-21-8 C₃₆H₄₀O₆ 
• 1448614-20-7 C₃₆H₃₉IO₆ 

Relevant academic research and scientific papers

Synthesis of C-septanosides from pyranoses via vinyl addition and electrophilic cyclization

A two-step synthesis of C-septanosides from pyranoses is reported. Vinyl addition to tetra-O-benzyl d-glucose, d-galactose, and d-mannose gave the corresponding allylic alcohols. Electrophilic cyclization followed by treatment with iodine gave iodomethyl C-septanosides suitable for substitution reactions. The cyclizations were diastereoselective, giving cis-1,2 configured C-septanosides. Selectivity is rationalized through a model for electrophilic additions that invokes the conformation of the allylic system. This new approach should be generally applicable to the synthesis of a variety of C-septanosides.

On the synthesis of vinyl and phenyl C-furanosides by stereospecific debenzylative cycloetherification

Open-chain benzyl-ether-protected polyols in which one of the alcohols is either allylic or benzylic are synthesised by addition of organometallic vinyl or phenyl reagents to benzyl-ether-protected carbohydrate hemiacetals. The diastereoselectivity of add

Stereospecific debenzylative cycloetherification of carbohydrate-derived allylic alcohols, ethers and esters to form vinyl C-furanosides

Benzyl ether protected polyhydroxylated alkene compounds containing allylic alcohol, ether or ester functionality undergo a stereospecific cyclisation reaction upon treatment with TFA-acetonitrile-toluene with inversion of configuration at the allylic position and loss of a benzyl ether to give tetrahydrofurans. The Royal Society of Chemistry.