((5-(5-Ethynyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy)-hydroxy-phosphoryl)acetic acid

Base Information

• Chemical Name: ((5-(5-Ethynyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy)-hydroxy-phosphoryl)acetic acid
• CAS No.: 117627-05-1
• Molecular Formula: C₁₃H₁₃N₂O₉P*2Na
• Molecular Weight: 418.208
• DSSTox Substance ID: DTXSID50922485
• Wikidata: Q82896018
• ChEMBL ID: CHEMBL3142990
• Mol file: 117627-05-1.mol

Synonyms:117627-05-1;((5-(5-Ethynyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy)-hydroxy-phosphoryl)acetic acid;117652-19-4;((5-(5-Ethynyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxytetrahydro-furan-2-ylmethoxy)-hydroxy-phosphoryl}acetic acid;CHEMBL3142990;DTXSID50922485;{[5-(5-Ethynyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryl}-acetic acid;1-{5-O-[(Carboxymethyl)(hydroxy)phosphoryl]-2-deoxypentofuranosyl}-5-ethynyl-4-hydroxypyrimidin-2(1H)-one;2-[[(2R,3S,5R)-5-(5-ethynyl-2,4-dioxo-pyrimidin-1-yl)-3-hydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]acetic acid

Chemical Property of ((5-(5-Ethynyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy)-hydroxy-phosphoryl)acetic acid

Chemical Property:

• XLogP3: -2.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 374.05151706
• Heavy Atom Count: 25
• Complexity: 724

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of ((5-(5-Ethynyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy)-hydroxy-phosphoryl)acetic acid

There total 4 articles about ((5-(5-Ethynyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy)-hydroxy-phosphoryl)acetic acid 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:

{[(2R,3S,5R)-3-Acetoxy-5-(5-ethynyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryl}-acetic acid ethyl ester → 5'-O-<(Carboxymethyl)hydroxyphosphinyl>-2'-deoxy-5-ethynyluridine Disodium Salt (117627-05-1) + 2'-deoxy-5-ethynyluridine (61135-33-9)

Guidance literature:

With sodium hydroxide; for 2h; Yields of byproduct given; Ambient temperature;

DOI:10.1021/jm00122a014

Reference yield:

3'-O-Acetyl-2'-deoxy-5-ethynyluridine (117626-99-0) → 5'-O-<(Carboxymethyl)hydroxyphosphinyl>-2'-deoxy-5-ethynyluridine Disodium Salt (117627-05-1)

Guidance literature:

Multi-step reaction with 2 steps

1: dicyclohexylcarbodiimide / pyridine / 72 h / Ambient temperature

2: 86 mg / 2 M NaOH / 2 h / Ambient temperature

With sodium hydroxide; dicyclohexyl-carbodiimide; In pyridine;

DOI:10.1021/jm00122a014

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-5-(1-phenyl-1H-1,2,3-triazol-4-yl)-2'-deoxyuridine (117626-97-8) → 5'-O-<(Carboxymethyl)hydroxyphosphinyl>-2'-deoxy-5-ethynyluridine Disodium Salt (117627-05-1)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 24 h

2: 0.16 g / 80percent aq. HOAc / 4.5 h

3: dicyclohexylcarbodiimide / pyridine / 72 h / Ambient temperature

4: 86 mg / 2 M NaOH / 2 h / Ambient temperature

With pyridine; sodium hydroxide; acetic acid; dicyclohexyl-carbodiimide; In pyridine;

DOI:10.1021/jm00122a014

upstream raw materials:

3'-O-Acetyl-2'-deoxy-5-ethynyluridine

5'-O-(4,4'-dimethoxytrityl)-5-(1-phenyl-1H-1,2,3-triazol-4-yl)-2'-deoxyuridine

3'-Acetyl-2'-deoxy-5-ethynyl-5'-(4,4'-dimethoxytrityl)uridine