3'-Methylamino-2',3'-dideoxyribosylthymine

Base Information

• Chemical Name: 3'-Methylamino-2',3'-dideoxyribosylthymine
• CAS No.: 141039-00-1
• Molecular Formula: C11H17 N3 O4
• Molecular Weight: 255.274
• DSSTox Substance ID: DTXSID10161535
• Wikidata: Q83029958
• Mol file: 141039-00-1.mol

Synonyms:3'-methylamino-2',3'-dideoxyribosylthymine;ddT(3'NHMe)

Chemical Property of 3'-Methylamino-2',3'-dideoxyribosylthymine

Chemical Property:

• PSA: 96.61000
• Density: 1.35g/cm3
• LogP: -0.48400
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 255.12190603
• Heavy Atom Count: 18
• Complexity: 396

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)NC
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)NC

Technology Process of 3'-Methylamino-2',3'-dideoxyribosylthymine

There total 7 articles about 3'-Methylamino-2',3'-dideoxyribosylthymine 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: 80.0%

5-Methyl-1-((2R,4S,5S)-4-methylamino-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione (153907-25-6) → 3'-N-methylamino-3'-deoxythymidine (141039-00-1)

Guidance literature:

With Dowex 50Wx₂ (H⁺); In methanol; water;

DOI:10.1080/07328319308018565

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3'-amino-3'-deoxythymidine (52450-18-7) → 3'-N-methylamino-3'-deoxythymidine (141039-00-1) + 3'-N,N-dimethylamino-3'-deoxythymidine

Guidance literature:

With sodium tetrahydroborate; Yield given. Multistep reaction. Yields of byproduct given; 1.) EtOH, room temperature, 48 h, 2.) 3 h;

DOI:10.1080/15257779508014650

Reference yield:

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-threo-pentofuranosyl)thymine (104218-44-2) → 3'-N-methylamino-3'-deoxythymidine (141039-00-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / sodium azide / ethane-1,2-diol / 0.75 h / 120 °C

2: 93 percent / sodium borohydride / propan-2-ol / 14 h / 82 °C

3: sodium acetate trihydrate, glacial acetic acid / ethanol; H₂O / 0.08 h / 0 - 5 °C

4: sodium borohydride / ethanol; H₂O

5: 80 percent / Dowex 50Wx₂ (H⁺) / methanol; H₂O

With sodium tetrahydroborate; sodium azide; Dowex 50Wx₂ (H⁺); sodium acetate; acetic acid; In methanol; ethanol; water; ethylene glycol; isopropyl alcohol;

DOI:10.1080/07328319308018565

upstream raw materials:

5-Methyl-1-((2R,4S,5S)-4-methylamino-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

formaldehyd

3'-amino-3'-deoxythymidine

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

Refernces

• 1、 Celewicz,Urjasz,Golankiewicz. "Synthesis of 3'-N-substituted 3'-amino-3'-deoxythymidine derivatives". . p. 951 - 966. Retrieved 2007/10/02.