169516-55-6

Basic information

• Product Name: 4-Chloro-7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-7H-pyrrolo[2.3-d]pyriMidine
• Synonyms: 4-Chloro-7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-7H-pyrrolo[2.3-d]pyriMidine;((2R,3R,4S,5R)-3-(Benzoyloxy)-5-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-fluorotetrahydrofuran-2-yl)methyl benzoate
• CAS NO: 169516-55-6
• Molecular Formula: C₂₅H₁₉ClFN₃O₅
• Molecular Weight: 495.8868632
• Mol File: 169516-55-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Chloro-7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-7H-pyrrolo[2.3-d]pyriMidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-7H-pyrrolo[2.3-d]pyriMidine(169516-55-6)
• EPA Substance Registry System: 4-Chloro-7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-7H-pyrrolo[2.3-d]pyriMidine(169516-55-6)

Safety Data

• Hazardous Substances Data: 169516-55-6(Hazardous Substances Data)

Upstream product

• 97614-44-3 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide 
• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 97614-43-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose 
• 52133-67-2 ethyl 2-cyano-4,4-diethoxybutyrate 
• 3680-71-5 1H-pyrrolo[2,3-d]pyrimidin-4(7H)-one 
• 67831-84-9 2-thioxo-1,2,3,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 7400-05-7 6-amino-5-(2,2-diethoxyethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one 
• 98855-71-1 ((2R,3R,4S)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate 

Downstream Products

• 1338072-77-7 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-(thiophen-3-yl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1338072-75-5 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-(furan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1338072-82-4 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-methyl-7H-pyrrolo[2,3-d]pyrimidine 
• 1338072-69-7 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-(furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1338072-72-2 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-(thiophen-2-yl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1338072-79-9 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-(thiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1338072-67-5 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-phenyl-7H-pyrrolo[2,3-d]pyrimidine 
• 1345193-54-5 C₂₅H₁₆Cl₂F₂N₆O₅ 
• 1345193-51-2 C₁₈H₁₂ClF₂IN₆O₃ 
• 1289376-75-5 C₁₈H₁₃ClFIN₆O₃ 
• 1289376-76-6 C₂₅H₁₇Cl₂FN₆O₅ 
• 169516-60-3 4-chloro-7-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine 

Relevant articles and documents

CYCLIC DINUCLEOTIDES AS ANTICANCER AGENTS

The present invention is directed to compounds of the formulae I, II and III as shown below wherein all substituents are defined herein, as well as pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

ANTIVIRAL AGENTS

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Sugar-modified derivatives of cytostatic 6-(het)aryl-7-deazapurine nucleosides: 2′-c-methylribonucleosides, arabinonucleosides and 2′-deoxy-2′-fluoroarabinonucleosides

A series of novel sugar-modified derivatives of cytostatic 6-hetaryl-7-deazapurine ribonucleo-sides: 2′-C-methylribonucleosides, arabinonucleosides and 2′-deoxy-2′-fluoroarabinonucleo-sides bearing an alkyl, aryl and hetaryl group in position 6 were prepared by palladium catalyzed cross-coupling reactions of corresponding (protected) 6-chloro-(7-fluoro)-7-deazapurine nucleosides with (het)arylboronic, hetarylstannanes and trimethylaluminium eventually followed by deprotection. Key intermediate 6-chloro-7-deazapurine 2′-C-methyl-β-D-ribofuranoside was prepared via a stereoselective nucleobase anion glycosylation with toluoyl-protected 1,2-anhydro-2-C-methylribofuranose. The 1,2-anhydro sugar was synthesized in 3 steps starting from readily available 2-C-methylribonolactone. The 6-chloro-7-deazapurine arabinofuranoside intermediate was obtained by epimerization from 3′,5′-protected 6-chloro-7-deazapurine ribofuranoside via 2′-hydroxyl oxidation followed by reduction. None of the prepared compounds showed any considerable cytostatic or antiviral activity.