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

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

• 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 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 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.

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.

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.

Radical Decarboxylative Alkylation onto Heteroaromatic Bases with Trivalent Iodine Compounds

Heteroaromatic bases containing nitrogen atoms were easily alkylated with carboxylic acids in the presence of benzene and pentafluorobenzene via radical pathways.Similarly, the alkylation onto heteroaromatic bases was carried out with oxalic acid monoalkyl esters, which were prepared from alcohols and oxalyl dichloride, in the presence of the same trivalent iodine compounds.Moreover, this system was applied to the synthesis of C-nucleosides with the carboxylic acids bearing a sugar moiety.

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.

Novel synthesis of C-Nucleosides via radical coupling reaction

Photolysis of O-acyl-N-hydroxy-2-thiopyridone, derived from 2-tetrahydrofuryl carboxylic acid or 2,5 -anhydro -D -allonic acid, gave the corresponding C-nucleoside derivatives in the presence of heteroaromatic compounds via radical pathways.