307306-11-2

Basic information

• Product Name: 5-fluoro-4-(β-D-glycero-pentofuran-3-ulos-1-yl)-2-methylaniline
• Synonyms: 5-fluoro-4-(β-D-glycero-pentofuran-3-ulos-1-yl)-2-methylaniline
• CAS NO: 307306-11-2
• Molecular Weight: 239.246
• Mol File: 307306-11-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-fluoro-4-(β-D-glycero-pentofuran-3-ulos-1-yl)-2-methylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-fluoro-4-(β-D-glycero-pentofuran-3-ulos-1-yl)-2-methylaniline(307306-11-2)
• EPA Substance Registry System: 5-fluoro-4-(β-D-glycero-pentofuran-3-ulos-1-yl)-2-methylaniline(307306-11-2)

Safety Data

• Hazardous Substances Data: 307306-11-2(Hazardous Substances Data)

Upstream product

• 452-51-7 D-2-deoxyribose 
• 367-29-3 3-fluoro-6-methylaniline 
• 90344-34-6 3,5-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-deoxy-D-ribose 
• 173327-56-5 3,5-bis-O,O-(tert-butyldimethylsilyl)-1,2-didehydro-1,2-dideoxy-D-ribofuranose 
• 34371-14-7 2-deoxy-D-ribonolactone 
• 307306-08-7 2-methyl-5-fluoro-4-iodoaniline 

Relevant articles and documents

Syntheses of 4-[1-(2-deoxy-β-D-ribofuranosyl)]-derivatives of 2-substituted-5-fluoroaniline: 'Cytosine replacement' analogs of deoxycytidine for evaluation as anticancer and antihuman immunodeficiency virus (anti-HIV) agents

A group of 4-[1-(2-deoxy-β-D-ribofuranosyl)]-derivatives of 5-fluoroaniline possessing a variety of aryl C-2 substituents (6a R = H, 6b R = F, 6c R = Me) were synthesized. Accordingly, a Heck-type coupling reaction of the 4-iodoaniline derivatives (13a-c) with the bis(tert-butyldimethylsilyl)glycal (11) in the presence of Pd(OAc)2 and Ph3As, followed by removal of the tert-butyldimethylsilyl protection groups using n-Bu4N+F-, yielded the corresponding 4-(β-D-glycero-pentofuran-3-ulos-1-yl)aniline derivatives (14a-c) having a C-3 C=O in the sugar ring. Reduction of the C-3 C=O compounds (14a-c) using NaB(OAc)3H afforded the target 4-[1-(2-deoxy-β-D-ribofuranosyl)]-derivatives of the respective 2-substituted-5-fluoroaniline (6a-c). The deoxycytidine mimic, 3-fluoro-4-[1-(2-deoxy-β-D-ribofuranosyl)]aniline (6a), in which the cytosine ring of deoxycytidine is replaced by a 4-(3-fluoroaniline) ring system, was inactive as an anticancer agent against a variety of tumor cell lines, and as an antihuman immunodeficiency virus (HIV-1, HIV-2) agent. The failure of this unnatural deoxycytidine mimic (6a) to exhibit anticancer-antiviral activity may be due to its inability to undergo phosphorylation by host cell- and virus-induced kinases.