3'-Amino-3'-deoxythymidine

Base Information

• Chemical Name: 3'-Amino-3'-deoxythymidine
• CAS No.: 52450-18-7
• Molecular Formula: C10H15N3O4
• Molecular Weight: 241.247
• UNII: 7W21M0C25B
• DSSTox Substance ID: DTXSID00966879
• Nikkaji Number: J263.917C
• Wikidata: Q27268932
• ChEMBL ID: CHEMBL103356
• Mol file: 52450-18-7.mol

Synonyms:3'-amino-2',3'-dideoxythymidine;3'-amino-3'-deoxythymidine;3'-aminothymidine

Chemical Property of 3'-Amino-3'-deoxythymidine

Chemical Property:

• Melting Point: 161-162 °C
• PKA: 9.55±0.10(Predicted)
• PSA: 110.34000
• Density: 1.36 g/cm³
• LogP: -0.84760
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Sparingly, Heated)
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 241.10625597
• Heavy Atom Count: 17
• Complexity: 382

Purity/Quality:

98%,99%, ^*data from raw suppliers

3’-Amino-3’-deoxythymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)N
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)N
• Uses: A metabolite of Zidovudine (3?Azido-3?deoxythymidine; AZT)

Technology Process of 3'-Amino-3'-deoxythymidine

There total 35 articles about 3'-Amino-3'-deoxythymidine 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: 99.0%

3'-azido-2',3'-deoxythymidine (30516-87-1,399024-19-2) → 3'-amino-3'-deoxythymidine (52450-18-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 2h;

DOI:10.3390/molecules26020320

Reference yield: 89.0%

1-((4S,5S)-4-(hydroxyamino)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (118466-35-6) → 3'-amino-3'-deoxythymidine (52450-18-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; In water; at 20 ℃; for 20h;

DOI:10.1021/acs.orglett.9b03474

Reference yield: 89.0%

5'-O-Acetyl-3'-deoxy-3'-phthalimidothymidine (100064-91-3) → 3'-amino-3'-deoxythymidine (52450-18-7)

Guidance literature:

With methylamine; In ethanol; for 2.5h; Heating;

DOI:10.1055/s-1989-27259

upstream raw materials:

3'-azido-2',3'-deoxythymidine

3'-amino-3'-deoxy-5'-O-triphenylmethyl-β-D-thymidine

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

5'-O-Acetyl-3'-deoxy-3'-phthalimidothymidine

Downstream raw materials:

methyl (2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-ylcarbamate

3',5'-oxazolidinone-3'-deoxythymidine

1-(2,3-dideoxy-3-(N-t-butyloxycarbonyl-L-alanylamino)-β-D-erythro-pentofuranosyl)thymine

3'-[(N-benzyloxycarbonyl-β-alanyl)-amino]-3'-deoxy-thymidine

Refernces

• 1、 Zheng, Qinheng,Xu, Hongtao,Wang, Hua,Du, Wen-Ge Han,Wang, Nan,Xiong, Huan,Gu, Yuang,Noodleman, Louis,Sharpless, K. Barry,Yang, Guang,Wu, Peng. "Sulfur [18F]Fluoride Exchange Click Chemistry Enabled Ultrafast Late-Stage Radiosynthesis". . p. 3753 - 3763. Retrieved 2021.
• 2、 Motawia,Wengel,Abdel-Megid,Pedersen. "A convenient route to 3'-amino-3'-deoxythymidine". . p. 384 - 387. Retrieved 1989.
• 3、 Pourshahian, Soheil,Gryaznov, Sergei M.. "Stereochemistry of internucleoside phosphorus atom affects sugar pucker and acid hydrolysis of N3′-P5′ thio-phosphoramidates". . . Retrieved 2021.
• 4、 Solyev, Pavel N.,Novikov, Roman A.,Kukhanova, Marina K.,Jasko, Maxim V.. "1,3-Dipolar cycloaddition of alkenes to 3'-azido-3'-deoxythymidine as a route to 3'-deoxythymidin-3'-yl derivatives". . p. 206 - 208. Retrieved 2014.
• 5、 Yuhas, Shelby C.,Laverty, Daniel J.,Lee, Huijin,Majumdar, Ananya,Greenberg, Marc M.. "Selective Inhibition of DNA Polymerase β by a Covalent Inhibitor". supporting information. p. 8099 - 8107. Retrieved 2021/06/21.