Brivudine monophosphate

Base Information

• Chemical Name: Brivudine monophosphate
• CAS No.: 80860-82-8
• Molecular Formula: C₁₁H₁₄BrN₂O₈P
• Molecular Weight: 413.119
• UNII: O7N0Y11U8K
• Nikkaji Number: J2.544.935E,J898.677K
• Wikidata: Q27285444
• Metabolomics Workbench ID: 148885
• ChEMBL ID: CHEMBL1231519
• Mol file: 80860-82-8.mol

Synonyms:5-(2-bromovinyl)-2'-deoxyuridylate;5-(2-bromovinyl)-2'-deoxyuridylate, (E)-isomer;BrvdUMP

Chemical Property of Brivudine monophosphate

Chemical Property:

• XLogP3: -2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 411.96711
• Heavy Atom Count: 23
• Complexity: 603

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)C=CBr)COP(=O)(O)O)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)/C=C/Br)COP(=O)(O)O)O

Technology Process of Brivudine monophosphate

There total 18 articles about Brivudine monophosphate 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: 79.0%

(E)-5-(2-bromovinyl)-2'-deoxyuridine (69304-47-8) → (E)-5-(2-bromovinyl)-2'-deoxyuridine 5'-monophosphate (80860-82-8)

Guidance literature:

With trimethyl phosphite; trichlorophosphate; at -5 ℃; for 20h;

DOI:10.1080/15257770802088787

Reference yield:

5'-O-tert-butyldimethylsilyl-(E)-5-(2-bromovinyl)-2'-deoxyuridine (376393-38-3) → (E)-5-(2-bromovinyl)-2'-deoxyuridine 5'-monophosphate (80860-82-8)

Guidance literature:

Multi-step reaction with 6 steps

1: DCC; DMAP / tetrahydrofuran / 3 h / 20 °C

2: TBAF / tetrahydrofuran / 3 h / 20 °C

3: DIPEA / 2 h / 20 °C

4: TBHP / acetonitrile / 0.25 h / 20 °C

5: TFA / CH₂Cl₂; methanol / 0.5 h / 20 °C

6: aq. phosphate buffer / 1.2 h / pH 7.3

With tert.-butylhydroperoxide; dmap; phosphate buffer; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1081/NCN-100002301

Reference yield:

(E)-5-(2-bromovinyl)-3'-O-acetyl-2'-deoxyuridine (84218-88-2) → (E)-5-(2-bromovinyl)-2'-deoxyuridine 5'-monophosphate (80860-82-8)

Guidance literature:

Multi-step reaction with 3 steps

1: DIPEA / 2 h / 20 °C

2: TBHP / acetonitrile / 0.25 h / 20 °C

3: aq. phosphate buffer / 11.3 h / pH 7.3

With tert.-butylhydroperoxide; phosphate buffer; N-ethyl-N,N-diisopropylamine; In acetonitrile;

DOI:10.1081/NCN-100002301

upstream raw materials:

cyclo(3-methylsaligenyl)-5'-O-((E)-5-(2-bromovinyl)-2'-deoxyuridinyl)phosphate

cyclo(3-methylsaligenyl)-5'-O-((E)-5-(2-bromovinyl)-3'-O-acetyl-2'-deoxyuridinyl)phosphate

cyclo(3-methylsaligenyl)-5'-O-((E)-5-(2-bromovinyl)-3'-O-hexanoyl-2'-deoxyuridinyl)phosphate

cyclo(3-methylsaligenyl)-5'-O-((E)-5-(2-bromovinyl)-2'-deoxy-3'-O-L-phenylalanyluridinyl)phosphate