90301-59-0

Basic information

• Product Name: 5-(2-chloroethyl)-1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl ]pyrimidine-2,4-dione
• Synonyms: 5-(2-chloroethyl)-1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl ]pyrimidine-2,4-dione;5-(2-chloroethyl)-2'-deoxyuridine
• CAS NO: 90301-59-0
• Molecular Formula: C₁₁H₁₅ClN₂O₅
• Molecular Weight: 290.7
• Mol File: 90301-59-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 161-164 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.485g/cm³
• PKA: 9.24±0.10(Predicted)
• CAS DataBase Reference: 5-(2-chloroethyl)-1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl ]pyrimidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-chloroethyl)-1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl ]pyrimidine-2,4-dione(90301-59-0)
• EPA Substance Registry System: 5-(2-chloroethyl)-1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl ]pyrimidine-2,4-dione(90301-59-0)

Safety Data

• Hazardous Substances Data: 90301-59-0(Hazardous Substances Data)

Upstream product

• 3056-12-0 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythropentofuranosyl chloride 
• 23956-12-9 5-(2-hydroxyethyl)-uracil 
• 90301-68-1 5-(2-Chloroethyl)uracil 
• 97975-00-3 5-(2-deoxy-β-D-erythro-pentofuranosyl)-2,3-dihydro-5H-furano<2,3-d>pyrimidin-6-one 
• 90301-69-2 5-(2-chloroethyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-1H,3H-pyrimidine-2,4-dione 
• 90301-60-3 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(2-hydroxyethyl)pyrimidine-2,4(1H,3H)-dione 

Downstream Products

• 115365-40-7 <5-(2-chloroethyl)-2'-deoxyuridin-5'-yl>(phenylamino)phosphinecarboxylic acid ethyl ester oxide 
• 115365-30-5 <(benzyloxy)carbonyl>phosphonic acid 5-(2-chloroethyl)-2'-deoxyuridin-5'-yl ester 
• 115365-33-8 5-(2-chloroethyl)-5'-(4,4'-dimethoxytrityl)-2'-deoxyuridine 

Relevant articles and documents

Syntheses of 5-(2-radiohaloethyl)- and 5-(2-radiohalovinyl)-2′-deoxyuridines. Novel types of radiotracer for monitoring cancer gene therapy with PET

Syntheses of 5-(2-[18F]fluoroethyl)- (1) 5-(2-[80Br] bromoethyl), (2), undeprotected (E)-5-(2-[18F]fluorovinyl)- (3) and (E)-5-(2-[80Br]bromovinyl),2′-deoxyuridines (4) as the tracers for monitoring cancer gene therapy with positron emission tomography were described. Decay corrected radiochemical yield and synthesis time including labeling and HPLC purification from end of bombardment for 1 was 9.5% and 2 hours, respectively; yield and time for 2 was 16% and 2 hours, respectively. Chemical (approximate to radiochemical) yield and time for synthesis of 3 was 7.5% and 7 minutes, respectively. Radiochemical yield and synthesis time including labeling and HPLC purification of an analytical sample of 4 was 60% and 30 minutes, respectively. Both 2 and 4 received the side reactions during HPLC purification, i.e. ring closure and cleavage of glycosidic bond, respectively. Application of 2 and 4 needed to be confirmed by in vitro or in vivo experiments. Radiochemical yield of 1 could be optimized by employing a modified protocol for preparation of its precursor. The preparation of fluorovinyl counterparts had demonstrated the potential utility of the stannane, 3-tolyl-3′,5′-di-O-acetyl-(E)-5-(2-stannylvinyl)- 2′-deoxyuridine 7. Copyright

5-(Haloalkyl)-2'-deoxyuridines: A Novel Type of Potent Antiviral Nucleoside Analogue

Syntheses of 5-(2-haloethyl)-2'-deoxyuridines, 5-(3-chloropropyl)-2'-deoxyuridines, and 5-(2-chloroethyl)-2'-deoxycytidine are described.The antiviral activities of these compounds were determined in cell culture against herpes simplex virus types 1 and 2