Thymidine, 2',3'-didehydro-3'-deoxy-, 5'-(hydrogen phosphonate)

Base Information

• Chemical Name: Thymidine, 2',3'-didehydro-3'-deoxy-, 5'-(hydrogen phosphonate)
• CAS No.: 140132-35-0
• Molecular Formula: C₁₀H₁₃N₂O₆P
• Molecular Weight: 288.197
• Wikidata: Q82906130
• Mol file: 140132-35-0.mol

Synonyms:d4T-HP;Thymidine, 2',3'-didehydro-3'-deoxy-, 5'-(hydrogen phosphonate);140132-35-0;[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxyphosphinic acid

Chemical Property of Thymidine, 2',3'-didehydro-3'-deoxy-, 5'-(hydrogen phosphonate)

Chemical Property:

• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 287.04329810
• Heavy Atom Count: 19
• Complexity: 488

Purity/Quality:

97% ^*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)C2C=CC(O2)CO[P+](=O)O
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C=C[C@H](O2)CO[P+](=O)O

Technology Process of Thymidine, 2',3'-didehydro-3'-deoxy-, 5'-(hydrogen phosphonate)

There total 1 articles about Thymidine, 2',3'-didehydro-3'-deoxy-, 5'-(hydrogen phosphonate) 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:

stavudin (3056-17-5) → C10H13N2O6P (140132-35-0)

Guidance literature:

With pyridine; phosphonic acid; pivaloyl chloride; at 20 ℃; for 0.0833333h;

DOI:10.1055/s-2004-815939

Reference yield:

C10H13N2O6P (140132-35-0) → O-benzyl-O'-(2',3'-didehydro-2',3'-dideoxythymidin-5'-yl) boranophosphate

Guidance literature:

Multi-step reaction with 3 steps

1.1: pivaloyl chloride; pyridine / 0.17 h / 20 °C

2.1: tetrahydrofuran / 1 h / 20 °C

2.2: i-Pr₂NEt*BH₃ / tetrahydrofuran / 1 h

3.1: aq. NH₃ / ethanol; tetrahydrofuran

With pyridine; ammonium hydroxide; pivaloyl chloride; In tetrahydrofuran; ethanol;

DOI:10.1055/s-2004-815939

Reference yield:

C10H13N2O6P (140132-35-0) → O-cyclohexyl-O'-(2',3'-didehydro-2',3'-dideoxythymidin-5'-yl) boranophosphate

Guidance literature:

Multi-step reaction with 3 steps

1.1: pivaloyl chloride; pyridine / 0.17 h / 20 °C

2.1: tetrahydrofuran / 1 h / 20 °C

2.2: i-Pr₂NEt*BH₃ / tetrahydrofuran / 1 h

3.1: aq. NH₃ / ethanol; tetrahydrofuran

With pyridine; ammonium hydroxide; pivaloyl chloride; In tetrahydrofuran; ethanol;

DOI:10.1055/s-2004-815939

upstream raw materials:

stavudin

Downstream raw materials:

O-benzyl-O'-(2',3'-didehydro-2',3'-dideoxythymidin-5'-yl) phosphonate

O-cyclohexyl-O'-(2',3'-didehydro-2',3'-dideoxythymidin-5'-yl) phosphonate