121353-89-7

Basic information

• Product Name: 1-(2-Fluoro-2,3-dideoxy-β-D-threo-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione
• Synonyms: 1-(2,3-Dideoxy-2-fluoro-β-D-threo-pentofuranosyl)thymine;1-(2-Fluoro-2,3-dideoxy-β-D-threo-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione;2'β-Fluoro-3'-deoxythymidine
• CAS NO: 121353-89-7
• Molecular Formula: C10H13FN2O4
• Molecular Weight: 244.2196232
• Mol File: 121353-89-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(2-Fluoro-2,3-dideoxy-β-D-threo-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-Fluoro-2,3-dideoxy-β-D-threo-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione(121353-89-7)
• EPA Substance Registry System: 1-(2-Fluoro-2,3-dideoxy-β-D-threo-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione(121353-89-7)

Safety Data

• Hazardous Substances Data: 121353-89-7(Hazardous Substances Data)

Upstream product

• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 69256-17-3 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine 
• 65-71-4 thymin 
• 136228-16-5 5-O-Benzoyl-2,3-dideoxy-2-fluoro-1-O-methyl-β-D-threo-pentofuranose 
• 136228-19-8 5-O-benzoyl-2,3-dideoxy-2-fluoro-α-D-arabinofuranosyl bromide 
• 121353-88-6 1-<5-O-(monomethoxytrityl)-2-fluoro-2-deoxy-β-D-arabinofuransosyl>thymine 
• 141249-36-7 1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)thymine 
• 121353-95-5 1-<5-O-(monomethoxytrityl)-2,3-dideoxy-2-fluoro-threo-pentofuranosyl>thymine 

Relevant articles and documents

2'-fluorofuranosyl derivatives and novel method of preparing 2'-fluoropyrimidine and 2'-fluoropurine nucleosides

A compound has the formula STR1 wherein R is selected from the group consisting of (C7 -C20)aroyl, (C6 -C20)aryl, aralkyl and alkylaryl, and (C1 -C10)alkyl-di(C6 -C20)aryl Si, R' is selected from the group consisting of (C1 -C10)alkyl, (C7 -C20)aroyl and (C2 -C12)acyl, all of which may be further substituted with O, S, N or alkyl, and R'" is selected from the group consisting of halogen, (C1 -C10)alkoxy, (C1 -C10)acyloxy, O-methane-sulfonyl and O-p-toluenesulfonyl. A composition of matter comprises 0.001 to 99.999 wt % of the above compound.

Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides

Several 2'-fluoroarabino-2',3'-dideoxy- and 2'-fluoro-2',3'-unsaturated 2',3'-dideoxy pyrimidine nucleoside analogues are reported. The saturated analogues 1-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)thymine (2'-threo-FddT, 33), 1-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)uracil (2'-threo-FddU, 22) were readily prepared from the corresponding 2'-deoxy-2'-fluoroarabinosyl nucleoside analogue by radical deoxygenation of the 3'-OH. The unsaturated compounds 1-(2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl)thymine (2'-Fd4T, 40) and 1-[5-O-(monomethoxytrityl)-2-fluoro-2,3-dideoxy-β-D-glycero -pent-2-enofuranosyl]uracil (39) were synthesized by an elimination reaction of the O-2,3'-anhydro-2'-fluoro-lyxo derivatives under basic conditions. The cytidine analogues 28 and 41 were prepared by amination of the corresponding uridine derivatives; compounds 28 and 41 were deprotected to give 1-(2,3-dideoxy-2-fluoro-β-D-arabinofuranosyl)cytidine (2'-threo-FddC, 29) and 1-(2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl)cytosine (2'-Fd4C, 42), respectively. All of these novel compounds were evaluated in vitro against human immunodeficiency virus (HIV) (LAV isolate). 2'-threo-FddC (29) was the most active of the newly synthesized substances against HIV with an ID50 of 0.8 μg/mL; ddC had an ID50 of 0.007 μg/mL. Because of its potency in the initial tests, 29 was further evaluated in both T cells and macrophage/monocyte cell lines, with several different isolates of HIV. Although 2'-threo-FddC (29) exhibited good antiviral activity in these systems, it was less active than AZT in these assays. At 1 μM the inhibition of CFU-GM by 29 was found to be 35-40%; this is slightly higher than seen with AZT.