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

Base Information

• Chemical Name: ((5-(2,4-Dioxo-5-vinyl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy)-hydroxy-phosphoryl)acetic acid
• CAS No.: 117626-80-9
• Molecular Formula: C₁₃H₁₅N₂O₉P*2Na
• Molecular Weight: 420.223
• DSSTox Substance ID: DTXSID00922475
• Wikidata: Q82896000
• ChEMBL ID: CHEMBL3142997
• Mol file: 117626-80-9.mol

Synonyms:117626-80-9;((5-(2,4-Dioxo-5-vinyl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy)-hydroxy-phosphoryl)acetic acid;((5-(2,4-Dioxo-5-vinyl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxytetrahydro-furan-2-ylmethoxy)-hydroxy-phosphoryl}acetic acid;117627-30-2;CHEMBL3142997;DTXSID00922475;{[5-(2,4-Dioxo-5-vinyl-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-ethenyl-4-hydroxypyrimidin-2(1H)-one;2-[[(2R,3S,5R)-5-(2,4-dioxo-5-vinyl-pyrimidin-1-yl)-3-hydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]acetic acid

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

Chemical Property:

• XLogP3: -2.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 376.06716712
• Heavy Atom Count: 25
• Complexity: 676

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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

There total 10 articles about ((5-(2,4-Dioxo-5-vinyl-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:

5-vinyl-2'-deoxyuridine (55520-67-7) → Sodium; {[(2R,3S,5R)-5-(2,4-dioxo-5-vinyl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryl}-acetate (117626-80-9)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 4.5 h

2: pyridine / 24 h

3: 80percent aq. HOAc / 4.5 h

4: dicyclohexylcarbodiimide / pyridine / 72 h / Ambient temperature

5: 2 M NaOH / 2 h / Ambient temperature

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

DOI:10.1021/jm00122a014

Reference yield:

3'-O-Acetyl-2'-deoxy-5-ethynyluridine (117626-99-0) → Sodium; {[(2R,3S,5R)-5-(2,4-dioxo-5-vinyl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryl}-acetate (117626-80-9)

Guidance literature:

Multi-step reaction with 8 steps

1: dicyclohexylcarbodiimide / pyridine / 72 h / Ambient temperature

2: 2 M NaOH / 2 h / Ambient temperature

3: H₂ / Lindlar catalyst (poisoned)

4: pyridine / 4.5 h

5: pyridine / 24 h

6: 80percent aq. HOAc / 4.5 h

7: dicyclohexylcarbodiimide / pyridine / 72 h / Ambient temperature

8: 2 M NaOH / 2 h / Ambient temperature

With pyridine; sodium hydroxide; hydrogen; acetic acid; dicyclohexyl-carbodiimide; Lindlar's catalyst; In pyridine;

DOI:10.1021/jm00122a014

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 → Sodium; {[(2R,3S,5R)-5-(2,4-dioxo-5-vinyl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryl}-acetate (117626-80-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 2 M NaOH / 2 h / Ambient temperature

2: H₂ / Lindlar catalyst (poisoned)

3: pyridine / 4.5 h

4: pyridine / 24 h

5: 80percent aq. HOAc / 4.5 h

6: dicyclohexylcarbodiimide / pyridine / 72 h / Ambient temperature

7: 2 M NaOH / 2 h / Ambient temperature

With pyridine; sodium hydroxide; hydrogen; acetic acid; dicyclohexyl-carbodiimide; Lindlar's catalyst; In pyridine;

DOI:10.1021/jm00122a014

upstream raw materials:

Acetic acid (2R,3S,5R)-5-(2,4-dioxo-5-vinyl-3,4-dihydro-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester

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

5-vinyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine

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