1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione
• CAS No.: 30516-87-1
• Molecular Formula: C10H13N5O4
• Molecular Weight: 267.244
• Hs Code.: 29349990
• NSC Number: 602670
• ChEMBL ID: CHEMBL178240
• Mol file: 30516-87-1.mol

Synonyms:NSC602670;3'-Azidothymidine;1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione;Timazid;399024-19-2;Zidovudine, AZT;1-[(2R,4R,5S)-4-AZIDO-5-(HYDROXYMETHYL)OXOLAN-2-YL]-5-METHYL-PYRIMIDINE-2,4-DIONE;Thymidine, 8CI,;Trizivir (Salt/Mix);CHEMBL178240;SCHEMBL13609910;component of Combivir (Salt/Mix);HBOMLICNUCNMMY-UHFFFAOYSA-N;HMS3369K15;HMS3656A20;BCP03622;3'-Azido-3'-deoxythymidine, 98%;HB4602;STL451000;STL454167;ZINC04164448;AKOS015949577;AKOS037482514;CCG-229922;NCGC00015044-03;NCGC00015044-04;NCGC00015044-05;NCGC00094963-01;NCGC00094963-02;NCI60_004566;FT-0601543;EN300-295526;1-(3-azido-2,3-dideoxypentofuranosyl)-2-hydroxy-5-methylpyrimidin-4(1H)-one;1-(3-azido-2,3-dideoxypentofuranosyl)-4-hydroxy-5-methylpyrimidin-2(1H)-one;1-[4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Chemical Property of 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione

Chemical Property:

• Appearance/Colour: Off -white crystalline powder
• Melting Point: 106-112 °C
• Refractive Index: 47 ° (C=1, H2O)
• Boiling Point: 410.43°C (rough estimate)
• PKA: pKa 9.53(H2O t = 25.0±0.1 I = 0.00) (Uncertain)
• Flash Point: 9℃
• PSA: 134.07000
• Density: 1.3382 (rough estimate)
• LogP: -0.74354
• Storage Temp.: −20°C
• Sensitive.: Light Sensitive & Hygroscopic
• Solubility.: H2O: 50 mg/mL
• Water Solubility.: 1-5 g/100 mL at 17 ºC
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 267.09675391
• Heavy Atom Count: 19
• Complexity: 484

Purity/Quality:

99% ^*data from raw suppliers

Azidothymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40-36/37/38-20/21/22
• Safety Statements: 36/37/39-45-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)N=[N+]=[N-]
• Description: Zidovudine, also known as azidothymidine (AZT), is an antiviral agent acting via reverse transcnptase inhibition. It was first launched in the U.K. and subsequently introduced in over a dozen countries for the management of severe manifestations of HIV infection. In patients with AIDS and ARC, zidovudine reduces the risk of opportunistic infections and prolongs survival time. In symptom-free patients it shows promise in halting further immunological deterioration.
• Uses: A potent and selective inhibitor of HIV-1 replication antibacterial Zidovudine is an antiretroviral drug that is clinically active against HIV-1 and is intended to treat HIV-infected patients. Zidovudine is an analog of thymidine that inhibits replication of the AIDS virus. It also turned into mono-, di-, and triphosphates by the same cellular enzymes that catalyze phosphorylation of thymidine and thymidine nucleosides. Zidovudine-triphosphate is then included in the terminal fragment of the growing chain of viral DNA by viral reverse transcriptase, thus causing the viral DNA chain to break apart in cells infected with the virus. Zidovudine has been authorized for treating patients with AIDS. It significantly prolongs the life of the patient, although it has a number of toxic effects. Synonyms of this drug are azidothymidine and retrovir.
• Indications: Zidovudine was the first agent to be used to prevent the transmission of HIV from a pregnant woman to her child. It was given to the mother at 14 to 34 weeks’ gestation and to the child for the first 6 weeks of life. Current combination therapies employ zidovudine with another NRTI and a protease inhibitor.
• Therapeutic Function: Antiviral, Antineoplastic
• Clinical Use: Treatment of HIV infection in adults and children (in combination with other antiretroviral drugs) Reduction of maternal transmission of HIV to the fetus
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: absorption reduced by clarithromycin; avoid concomitant use with rifampicin. Antiepileptics: phenytoin levels may be raised or lowered; concentration possibly increased by valproate (increased risk of toxicity). Antifungals: concentration increased by fluconazole. Antivirals: profound myelosuppression with ganciclovir and valganciclovir - avoid if possible; increased risk of granulocytopenia with nevirapine; increased risk of anaemia with ribavirin - avoid; effects of stavudine inhibited - avoid concomitant use; concentration reduced by tipranavir. Orlistat: absorption possibly reduced by orlistat. Probenecid: excretion reduced by probenecid, increased risk of toxicity.

Technology Process of 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione

There total 169 articles about 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine (29706-84-1) → 3'-azido-2',3'-deoxythymidine (30516-87-1,399024-19-2)

Guidance literature:

With silica gel; trifluoroacetic acid; In methanol; chloroform;

DOI:10.1016/S0040-4039(01)01645-8

Reference yield: 95.0%

3'-azido-5'-O-benzoyl-3'-deoxythymidine (106060-78-0) → 3'-azido-2',3'-deoxythymidine (30516-87-1,399024-19-2)

Guidance literature:

With sodium methylate; In methanol; for 24h; Ambient temperature;

DOI:10.1007/BF02494517

Reference yield: 86.0%

3'-azido-3'-deoxy-5'-O-pivaloylthymidine → 3'-azido-2',3'-deoxythymidine (30516-87-1,399024-19-2)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1h;

upstream raw materials:

5'-O-trityl-2,3'-anhydrothymidine

1-(5′-O-acetyl-3′-azido-2′,3′-dideoxy-β-D-ribofuranosyl)thymine

3‘-azido-2’,3’-dideoxy-5’-O-(tetradecanoyl)thymidine

Downstream raw materials:

(4-Phenyl-piperazin-1-yl)-acetic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

(S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Phosphoric acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-chloro-phenyl ester 2-phenoxy-ethyl ester

Phosphoric acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-chloro-phenyl ester 2-(naphthalen-1-yloxy)-ethyl ester

Refernces

• 1、 Yanvarev, Dmitry V.,Shirokova, Elena A.,Astapova, Maria V.,Skoblov, Yury S.. "AZT 5′-cholinephosphate as an anti-HIV agent: The study of biochemical properties and metabolic transformations using its 32P-labelled counterpart". . p. 23 - 36. Retrieved 2007.
• 2、 Wiebe,Knaus,Cheraghali,Kumar,Morin,Wang. "5-Halo-6-alkoxy-5,6-dihydro-pyrimidine nucleosides: Antiviral nucleosides or nucleoside prodrugs?". . p. 501 - 505. Retrieved 1995.
• 3、 -. "Synthesis method of (1 beta, 2 alpha, 4 beta) halogenated nucleoside compound". Paragraph 0094-0096. . Retrieved 2022/01/12.
• 4、 Meng, Genyi,Guo, Taijie,Ma, Tiancheng,Zhang, Jiong,Shen, Yucheng,Sharpless, Karl Barry,Dong, Jiajia. "Modular click chemistry libraries for functional screens using a diazotizing reagent". . p. 86 - 89. Retrieved 2019/11/13.