N-{9-{5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-α-D-ribofuranosyl}-9H-purin-2-yl}acetamide

Base Information

• Chemical Name: N-{9-{5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-α-D-ribofuranosyl}-9H-purin-2-yl}acetamide
• CAS No.: 312745-80-5
• Molecular Formula: C₃₃H₃₃N₅O₆
• Molecular Weight: 595.655
• Mol file: 312745-80-5.mol

Synonyms:N-{9-{5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-α-D-ribofuranosyl}-9H-purin-2-yl}acetamide

Chemical Property of N-{9-{5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-α-D-ribofuranosyl}-9H-purin-2-yl}acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{9-{5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-α-D-ribofuranosyl}-9H-purin-2-yl}acetamide

There total 5 articles about N-{9-{5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-α-D-ribofuranosyl}-9H-purin-2-yl}acetamide 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: 38.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + N-[7-(2'-deoxy-α/β-D-ribofuranosyl)-7H-purin-2-yl]acetamide (312745-79-2) → N-{9-{5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-α-D-ribofuranosyl}-9H-purin-2-yl}acetamide + N-{9-{5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-α-D-ribofuranosyl}-9H-purin-2-yl}acetamide (312745-80-5)

Guidance literature:

In pyridine; for 18h;

DOI:10.1002/1522-2675(20000906)83:9<2514::AID-HLCA2514>3.0.CO;2-X

Reference yield:

N-(6-chloro-7(9)H-purin-2-yl)-acetamide (7602-01-9) → N-{9-{5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-α-D-ribofuranosyl}-9H-purin-2-yl}acetamide (312745-80-5)

Guidance literature:

Multi-step reaction with 5 steps

1: acetonitrile / 1 h / 60 °C

2: 77 percent / SnCl₄ / acetonitrile / 2.5 h / 0 - 20 °C

3: 84 percent / Et₃N; H₂ / Pd/C / ethyl acetate / 3 h / 20 °C / 750.06 Torr

4: 100 percent / NH₃ / methanol / 18 h / -20 - 20 °C

5: 25 percent / pyridine / 18 h

With ammonia; hydrogen; tin(IV) chloride; triethylamine; palladium on activated charcoal; In pyridine; methanol; ethyl acetate; acetonitrile; 1: silylation / 2: Condensation / 3: Dehalogenation / 4: Deacetylation / 5: Condensation;

DOI:10.1002/1522-2675(20000906)83:9<2514::AID-HLCA2514>3.0.CO;2-X

Reference yield:

N-(6-chloro-9-trimethylsilylpurin-2-yl)acetamide → N-{9-{5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-α-D-ribofuranosyl}-9H-purin-2-yl}acetamide (312745-80-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / SnCl₄ / acetonitrile / 2.5 h / 0 - 20 °C

2: 84 percent / Et₃N; H₂ / Pd/C / ethyl acetate / 3 h / 20 °C / 750.06 Torr

3: 100 percent / NH₃ / methanol / 18 h / -20 - 20 °C

4: 25 percent / pyridine / 18 h

With ammonia; hydrogen; tin(IV) chloride; triethylamine; palladium on activated charcoal; In pyridine; methanol; ethyl acetate; acetonitrile; 1: Condensation / 2: Dehalogenation / 3: Deacetylation / 4: Condensation;

DOI:10.1002/1522-2675(20000906)83:9<2514::AID-HLCA2514>3.0.CO;2-X

upstream raw materials:

4,4'-dimethoxytrityl chloride

N-[7-(2'-deoxy-α/β-D-ribofuranosyl)-7H-purin-2-yl]acetamide

N-(6-chloro-7⁽⁹⁾H-purin-2-yl)-acetamide

N-[7-(3',5'-di-O-acetyl-2'-deoxy-α/β-D-ribofuranosyl)-7H-purin-2-yl]acetamide