(E)-5-(2-bromovinyl)-3'-O-(N-Boc-D-phenylalaninyl)-2'-deoxyuridine

Base Information

• Chemical Name: (E)-5-(2-bromovinyl)-3'-O-(N-Boc-D-phenylalaninyl)-2'-deoxyuridine
• CAS No.: 476446-31-8
• Molecular Formula: C₂₅H₃₀BrN₃O₈
• Molecular Weight: 580.433
• Mol file: 476446-31-8.mol

Synonyms:(E)-5-(2-bromovinyl)-3'-O-(N-Boc-D-phenylalaninyl)-2'-deoxyuridine

Chemical Property of (E)-5-(2-bromovinyl)-3'-O-(N-Boc-D-phenylalaninyl)-2'-deoxyuridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-5-(2-bromovinyl)-3'-O-(N-Boc-D-phenylalaninyl)-2'-deoxyuridine

There total 2 articles about (E)-5-(2-bromovinyl)-3'-O-(N-Boc-D-phenylalaninyl)-2'-deoxyuridine 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-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester → (E)-5-(2-bromovinyl)-3'-O-(N-Boc-D-phenylalaninyl)-2'-deoxyuridine (476446-31-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1021/jm0209275

Reference yield:

5'-O-tert-butyldimethylsilyl-(E)-5-(2-bromovinyl)-2'-deoxyuridine (376393-38-3) → (E)-5-(2-bromovinyl)-3'-O-(N-Boc-D-phenylalaninyl)-2'-deoxyuridine (476446-31-8)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With dmap; tetrabutyl ammonium fluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm0209275

Reference yield:

3-methylsalicylchlorophosphane (192752-93-5) + (E)-5-(2-bromovinyl)-3'-O-(N-Boc-D-phenylalaninyl)-2'-deoxyuridine (476446-31-8) → 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-4H-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-3-yl ester

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at -20 ℃; for 0.333333h;

DOI:10.1021/jm0209275

upstream raw materials:

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