136409-52-4

Basic information

• Product Name: 4-methyl-2-(2',3',5'-tri-O-benzyl-α-D-ribofuranosyl)quinoline
• CAS NO: 136409-52-4
• Molecular Weight: 545.678
• Mol File: 136409-52-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4-methyl-2-(2',3',5'-tri-O-benzyl-α-D-ribofuranosyl)quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyl-2-(2',3',5'-tri-O-benzyl-α-D-ribofuranosyl)quinoline(136409-52-4)
• EPA Substance Registry System: 4-methyl-2-(2',3',5'-tri-O-benzyl-α-D-ribofuranosyl)quinoline(136409-52-4)

Safety Data

• Hazardous Substances Data: 136409-52-4(Hazardous Substances Data)

Upstream product

• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 42890-06-2 1-(2,3,5-Tri-O-benzyl)-D-ribofuranosylcarboxylic acid 
• 138809-95-7 2,3,5-tri-O-benzyl-α-D-ribofuranosylmethanoic acid 
• 42890-06-2 (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carboxylic acid 
• 52492-43-0 2,5-anhydro-3,4,6-tri-O-benzyl-D-allononitrile 
• 213202-76-7 Methanesulfonic acid (3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl ester 
• 16838-89-4 2,3,5-tri-O-benzyl-D-ribofuranose 
• 143671-61-8 4-methylquinoline trifluoroacetate 
• 194716-02-4 (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(4-methoxy-phenyltellanyl)-tetrahydro-furan 
• 213202-70-1 (2R,3R,4R,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(4-methoxy-phenyltellanyl)-tetrahydro-furan 

Relevant articles and documents

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.

Synthesis of C-Nucleosides via Radical Coupling Reaction

Photolysis of O-acyl derivatives of N-hydroxy-2-thiopyridone, prepared from tetrahydrofuran-2-carboxylic acid, D-ribofuranosylmethanoic acid, and D-ribopyranosylmethanoic acid, gave the corresponding C-nucleoside derivatives in the presence of heteroaromatic compounds via radical pathways.The essential step in this method is a radical coupling reaction of D-ribofuranosyl radical or D-ribopyranosyl radical and some heteroaromatic bases.This is a new method for the preparation of C-nucleosides using sugar carboxylic acids.

FACILE RADICAL DECARBOXYLATIVE ALKYLATION OF HETEROAROMATIC BASES USING CARBOXYLIC ACIDS AND TRIVALENT IODINE COMPOUNDS

Many kinds of heteroaromatic bases were easily alkylated by the reaction of carboxylic acids with benzene or pentafluorobenzene via radical decarboxylative pathways.This system was further applied to the reaction with tetrahydrofurylcarboxylic acid, 1-(2,3,5-tri-O-benzyl)-D-ribofuranosylacetic acid, and 1-(2,3,5-tri-O-benzyl)-D-ribofuranosylcarboxylic acid for the model synthesis of C-nucleosides.