183001-73-2

Upstream product

• 40899-71-6 1-benzenesulfonylindole 
• 86883-42-3 2,3,5-tris-O-(phenylmethyl)-β-D-ribofuranosyl fluoride 
• 213202-70-1 (2R,3R,4R,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(4-methoxy-phenyltellanyl)-tetrahydro-furan 
• 194716-02-4 (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(4-methoxy-phenyltellanyl)-tetrahydro-furan 
• 16838-89-4 2,3,5-tri-O-benzyl-D-ribofuranose 
• 213202-76-7 Methanesulfonic acid (3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl ester 

Relevant academic research and scientific papers

Application of the versatile character of the tellurium atom for the synthesis of C-nucleoside analogues via sugar tellurides

Making use of the versatile character of the tellurium atom such as its radicophilicity, nucleophilicity and electrophilicity, D-ribofuranosyl, 2-deoxy-D-ribofuranosyl and D-glucosyl p-methoxyphenyl tellurides have been prepared. Under suitable conditions, the corresponding anomeric radical, anomeric cation and anomeric anion, respectively, are formed from the sugar tellurides. By the following coupling reactions of the anomeric radical and anomeric cation to electron-poor and electron-rich aromatics, respectively, the corresponding C-nucleoside analogues have been synthesized in moderate yields. The anomeric anion has also been trapped by an electrophile such as benzaldehyde.

Strategic approach to C-nucleosides via sugar anomeric radical, cation, and anion with sugar tellurides

Direct coupling reactions of the protected D-ribofuranosyl p-anisyl telluride and 2-deoxy-D-ribofuranosyl p-anisyl telluride with electron-poor heteroaromatics and electron-rich aromatics via anomeric radical, cation, and anion were carried out.

Coupling of ribofuranosyl fluoride and indoles

The coupling reaction of a D-ribofuranosyl fluoride with indoles in the presence of boron trifluoride gives the corresponding C-nucleosides in a stereoselective manner depending upon reaction temperatures and solvents: the β-anomer is preferred under such conditions as -15 to -40°C in nitroethane while the α-anomer is preferred at -78°C in propiononitrile.