5'-[N⁴-(allyloxycarbonyl)cytosine arabinosyl] benzyl N-methyl-N-(4-chlorobutyl) phosphoramidate

Base Information

• Chemical Name: 5'-[N⁴-(allyloxycarbonyl)cytosine arabinosyl] benzyl N-methyl-N-(4-chlorobutyl) phosphoramidate
• CAS No.: 727399-10-2
• Molecular Formula: C₂₅H₃₄ClN₄O₉P
• Molecular Weight: 600.993
• Mol file: 727399-10-2.mol

Synonyms:5'-[N⁴-(allyloxycarbonyl)cytosine arabinosyl] benzyl N-methyl-N-(4-chlorobutyl) phosphoramidate

Chemical Property of 5'-[N⁴-(allyloxycarbonyl)cytosine arabinosyl] benzyl N-methyl-N-(4-chlorobutyl) phosphoramidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-[N⁴-(allyloxycarbonyl)cytosine arabinosyl] benzyl N-methyl-N-(4-chlorobutyl) phosphoramidate

There total 3 articles about 5'-[N⁴-(allyloxycarbonyl)cytosine arabinosyl] benzyl N-methyl-N-(4-chlorobutyl) phosphoramidate 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: 68.0%

benzyl alcohol (100-51-6,185532-71-2) + 5'-[N4-(allyloxycarbonyl)cytosine arabinosyl] 1-benzotriazolyl N-methyl-N-(4-chlorobutyl) phosphoramidate (727399-07-7) → 5'-[N4-(allyloxycarbonyl)cytosine arabinosyl] benzyl N-methyl-N-(4-chlorobutyl) phosphoramidate (727399-10-2)

Guidance literature:

With dmap; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ol049267j

Reference yield:

N4-(allyloxycarbonyl)cytosine arabinoside → 5'-[N4-(allyloxycarbonyl)cytosine arabinosyl] benzyl N-methyl-N-(4-chlorobutyl) phosphoramidate (727399-10-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 680 mg / N-methylimidazole; pyridine / tetrahydrofuran / 6 h / 20 °C

2: 68 percent / DMAP / tetrahydrofuran / 20 °C

With pyridine; 1-methyl-1H-imidazole; dmap; In tetrahydrofuran;

DOI:10.1021/ol049267j

Reference yield:

(4-chloro-butyl)-methyl-phosphoramidic acid dibenzotriazol-1-yl ester → 5'-[N4-(allyloxycarbonyl)cytosine arabinosyl] benzyl N-methyl-N-(4-chlorobutyl) phosphoramidate (727399-10-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 680 mg / N-methylimidazole; pyridine / tetrahydrofuran / 6 h / 20 °C

2: 68 percent / DMAP / tetrahydrofuran / 20 °C

With pyridine; 1-methyl-1H-imidazole; dmap; In tetrahydrofuran;

DOI:10.1021/ol049267j

upstream raw materials:

benzyl alcohol

5'-[N⁴-(allyloxycarbonyl)cytosine arabinosyl] 1-benzotriazolyl N-methyl-N-(4-chlorobutyl) phosphoramidate

Downstream raw materials:

5'-cytosine arabinosyl benzyl N-methyl-N-(4-chlorobutyl)phosphoramidate

2'-aracytidine 5'-triphosphate

Refernces