15379-29-0

Usage

Uses

Used in Pharmaceutical Industry:
5-fluoro-1-[(2S,5R)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidine-2,4-dione is used as a synthetic intermediate for the production of various pharmaceuticals, including antiviral and antineoplastic agents. Its unique structure and specific stereochemistry make it a valuable component in the synthesis of nucleoside analogs and other bioactive compounds.
Used in Antiviral Applications:
5-fluoro-1-[(2S,5R)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidine-2,4-dione is used as a key building block in the synthesis of antiviral agents. Its fluoropyrimidine structure allows for the development of drugs that target viral replication and inhibit viral growth.
Used in Antineoplastic Applications:
5-fluoro-1-[(2S,5R)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidine-2,4-dione is used as a precursor in the synthesis of antineoplastic agents. Its unique structure and specific stereochemistry enable the development of drugs that target cancer cells and inhibit tumor growth.
Used in Bioactive Compounds Synthesis:
5-fluoro-1-[(2S,5R)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidine-2,4-dione is used as a building block for the synthesis of nucleoside analogs and other bioactive compounds. Its pyrimidine ring and dihydrofuran moiety with a hydroxymethyl group contribute to the development of novel therapeutic agents with potential applications in various diseases and conditions.

Upstream product

• 34393-72-1 2,3'-anhydro-2'-deoxy-5-fluoro-1-(β-D-threo-pentofuranosyl)uracil 
• 144989-65-1 1-(3,5-anhydro-2-deoxy-β-D-threo-pentofuranosyl)-5-fluorouracil 
• 42867-74-3 1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-uracil 
• 50-91-9 5-Fluoro-2'-deoxyuridine 
• 7239-42-1 β-D-2'-deoxy-3',5'-di-O-mesyl-5-fluorouridine 
• 144989-67-3 2,3'-anhydro-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-5-fluoro-1-(β-D-threo-pentofuranosyl)uracil 
• 172473-14-2 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)-5-fluorouracil 
• 160203-74-7 1-(5'-O-acetyl-2',3'-didehydro-2',3'-dideoxy-β-D-ribofuranosyl)-5-fluorouracil 

Relevant academic research and scientific papers

Synthesis of 2,3'-anhydro-2'-deoxyuridines and 2,3'-didehydro-2',3'-dideoxyuridines using polymer supported fluoride

Reaction of methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-α,β-D-eryt hro-pentofuranoside (2) with silylated uracils 3 using trimethylsilyl trifluoromethanesulfonate (TMS triflate) as catalyst afforded after crystallization in Et2O the corresponding β-nucleosides 4. Reaction of 4 with tetrabutylammonium fluoride (TBAF) or Amberlyst A-26 resin (F--form) in THF at room temperature or at reflux gave the corresponding deprotected 2,3'-anhydro-2'-deoxyuridines 6 and 2',3'-didehydro-2',3'-dideoxyuridines 7, respectively.

The synthesis of difluoro and trifluoro analogues of pyrimidine deoxyribonucleosides: a novel approach using elemental fluorine

The preparation of some novel fluorodeoxy nucleosides in good yields by the fluorination of unsaturated intact nucleosides with elemental fluorine at -78 deg C in mixtures of chloroform, ethanol and fluorotrichloromethane is described.This is the first example of the fluorination of an intact nucleoside by elemental fluorine and represents a considerable step forward in the use of the element in the synthesis of bioactive species.Thus, we were able to obtain 1-(2',3'-didehydro-2',3'-dideoxy-β-D-ribofuranosyl)-5-fluorouracil (6), 1-(2',3'-didehydro-2',3'-dideoxy-2',3'-difluoro-β-D-ribofuranosyl)-5-fluorouracil (7), 1-(2',3'-didehydro-2',3'-dideoxy-2-fluoro-β-D-ribofuranosyl)-5-fluorouracil (8), 1-(2',3'-dideoxy-2',3'-difluoro-β-D-ribofuranosyl)-5-fluorocytosine (10), 2',3'-dideoxy-5-fluorouridine (11), 1-(2',3'-dideoxy-2'-fluoro-β-D-arabinofuranosyl)-5-fluorouracil (12), 1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-5-fluorouracil (13), 1-(2-deoxy-3,5-di-O-acetyl-β-D-ribofuranosyl)-5-fluorouracil (14) and (5R,6S)- and (5S,6R)-1-(3',5'-anhydro-2-deoxy-β-D-threo-pentofuranosyl)-difluoro-5,6-dihydro-5-methyluracil (16 and 17) by a series of fluorinations and deprotections.From the products we have obtained, it is clear that (at least in these fluorinations) the addition of the fluorine is in a cis mode.

Conversion of Some Pyrimidine 2'-Deoxyribonucleosides into the Corresponding 2',3'-Didehydro-2',3'-dideoxynucleosides

Thymidine 4b was converted into 2,3'-anhydro-1-(2'-deoxy-β-D-threo-pentofuranosyl)thymine 7b in ca. 65percent isolated yield by being heated at 155 deg C with an excess of diphenyl sulfite and 1-methylimidazole in N,N-dimethylacetamide solution. 2'-Deoxyuridine 4a, 2'-deoxy-5-ethyluridine 4c and 2'-deoxy-5-fluorouridine 4d were similarly converted into 2,3'-anhydronucleosides which were isolated as their 5'-O-(tert-butyldimethylsilyl) derivatives 8a, 8c and 8d in 51, 50 and 59percent yield, respectively.When the oxetane derivatives 5a-d, prepared by the literature procedure from the parent 2'-deoxynucleosides 4a-d, were heated with an excess of sodium hydride in N,N-dimethylacetamide solution at 100 deg C, they were converted into the corresponding 2',3'-didehydro-2',3'-dideoxynucleosides 6a-d in 68, 76, 69 and 74percent isolated yield, respectively.The latter compounds were similarly prepared from the 2,3'-anhydronucleosides 7a-d in 71, 81, 69 and 74percent isolated yield, respectively. 2,3'-Anhydro-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-5-(trifluoromethyl)- and -5-iodo-1-(β-D-threo-pentofuranosyl)uracil 8e and 8f, which were themselves prepared from the parent 2'-deoxynucleosides 4e and 4f, respectively, in ca. 60 and 50percent yield, were converted by a three-step procedure via the intermediate 2'-deoxy-3'-(phenylseleno) derivatives 10e and 10f into the corresponding 2',3'-didehydro-2',3'-dideoxynucleosides 6e and 6f in 52 and 49percent overall yield, respectively.Compound 8e was also converted into 2',3'-dideoxy-5-(trifluoromethyl)uridine 11b and 3'-azido-2',3'-dideoxy-5-(trifluoromethyl)uridine 11c in 49 and 66percent overall yield, respectively.