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

Base Information

• Chemical Name: cyclo(3-methylsaligenyl)-5'-O-((E)-5-(2-bromovinyl)-2'-deoxy-3'-O-L-phenylalanyluridinyl)phosphate
• CAS No.: 345233-97-8
• Molecular Formula: C₂₈H₂₉BrN₃O₉P
• Molecular Weight: 662.431
• Mol file: 345233-97-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about cyclo(3-methylsaligenyl)-5'-O-((E)-5-(2-bromovinyl)-2'-deoxy-3'-O-L-phenylalanyluridinyl)phosphate 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:

2-tert-butoxycarbonylamino-3-phenyl-propionic acid 5-[5-(2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2-(8-methyl-2-oxo-4H-2λ5-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-3-yl ester → cyclo(3-methylsaligenyl)-5'-O-((E)-5-(2-bromovinyl)-2'-deoxy-3'-O-L-phenylalanyluridinyl)phosphate (345233-97-8)

Guidance literature:

With trifluoroacetic acid; In methanol; dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1081/NCN-100002301

Reference yield:

3-methylsalicylchlorophosphane (192752-93-5) → cyclo(3-methylsaligenyl)-5'-O-((E)-5-(2-bromovinyl)-2'-deoxy-3'-O-L-phenylalanyluridinyl)phosphate (345233-97-8)

Guidance literature:

Multi-step reaction with 3 steps

1: diisopropylethylamine / acetonitrile / 0.33 h / -20 °C

2: tert-butyl hydroperoxide / acetonitrile / 0.5 h / -20 - 20 °C

3: trifluoroacetic acid / acetonitrile / 1.5 h / 20 °C

With tert.-butylhydroperoxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In acetonitrile;

DOI:10.1021/jm0209275

Reference yield:

(E)-5-(2-bromovinyl)-2'-deoxyuridine (69304-47-8) → cyclo(3-methylsaligenyl)-5'-O-((E)-5-(2-bromovinyl)-2'-deoxy-3'-O-L-phenylalanyluridinyl)phosphate (345233-97-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / pyridine / 14 h / 20 °C

2: (dimethylamino)pyridine; dicyclohexylcarbodiimide / CH₂Cl₂ / 0.5 h / 20 °C

3: tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C

4: diisopropylethylamine / acetonitrile / 0.33 h / -20 °C

5: tert-butyl hydroperoxide / acetonitrile / 0.5 h / -20 - 20 °C

6: trifluoroacetic acid / acetonitrile / 1.5 h / 20 °C

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

DOI:10.1021/jm0209275

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

(E)-5-(2-bromovinyl)-2'-deoxyuridine

3-methylsalicylchlorophosphane

5'-O-tert-butyldimethylsilyl-(E)-5-(2-bromovinyl)-2'-deoxyuridine

Downstream raw materials:

(E)-5-(2-bromovinyl)-2'-deoxyuridine 5'-monophosphate