198271-82-8

Upstream product

• 64-17-5 ethanol 
• 198271-81-7 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl isothiocyanate 
• 153923-40-1 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl bromide 
• 138811-45-7 1,2,3,5,6-penta-O-benzoyl-D-galactofuranose 
• 201738-27-4 C₃₄H₂₇ClO₉ 

Relevant academic research and scientific papers

Reactions of per-O-benzoyl-β-D-galf isothiocyanate, a chiral resolving agent

Tetra-O-benzoyl-β-D-galactofuranosyl isothiocyanate (1) was readily prepared (90% yield) from per-O-benzoyl-D-galactofuranose, via the glycosyl bromide. Reaction of 1 with alcohols, amines and amino acids afforded a variety of glycosylthiourethanes and glycosylthioureides. The isothiocyanate 1 showed to be useful as a chiral resolving agent. The resolution of recemic primary and secondary mines and aminoalcohols was readily accomplished, in analytical and preparative scale, by condensation of such compounds with 1.

Synthesis of β-D-galactofuranosyl nucleoside analogues. A new type of β-D-galactofuranosidase inhibitor

The development of β-D-galactofuranosidase inhibitors provides a good chemotherapeutic target for treatment of major human diseases, because β-D-galactofuranose is a constituent of important pathogen microorganisms but is absent in mammals. With this purpose we have prepared β-D-galactofuranosyl nucleoside analogues, derived by the addition of nucleophiles to perbenzoylated β-D-galactofuranosyl isothiocyanate, a compound previously prepared in this laboratory. N-β-D-Galactofuranosyl-O-ethylthiourethane, N-β-D-galactofuranosyl-4-oxoimidazolidine-2-thione, N-β-D-galactofuranosyl-4-imidazoline-2-thione, and N-β-D-galactofuranosyl-4-methoxyimidazolidine-2-thione, were prepared. The biological assays showed that imidazoline and imidazolidine-2-thione derivatives act as a new type of exo β-D-galactofuranosidase inhibitor.

Facile synthesis of glycofuranosyl isothiocyanates

Peracylated glycofuranosyl isothiocyanates are obtained under smooth conditions starting from the corresponding glycosyl chloride by reaction with potassium thiocyanate in anhydrous acetone at room temperature, classical conditions for the synthesis of gl