N-{9-((2R,3R,4S,5R)-3-Hydroxy-4-trityloxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-acetamide

Base Information

• Chemical Name: N-{9-((2R,3R,4S,5R)-3-Hydroxy-4-trityloxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-acetamide
• CAS No.: 144588-13-6
• Molecular Formula: C₅₈H₅₀N₆O₈
• Molecular Weight: 959.07
• Mol file: 144588-13-6.mol

Synonyms:

Chemical Property of N-{9-((2R,3R,4S,5R)-3-Hydroxy-4-trityloxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{9-((2R,3R,4S,5R)-3-Hydroxy-4-trityloxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-acetamide

There total 3 articles about N-{9-((2R,3R,4S,5R)-3-Hydroxy-4-trityloxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-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: 50.0%

trityl chloride (76-83-5) + N-{9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-acetamide (144588-12-5) → N-{9-((2R,3R,4S,5R)-3-Hydroxy-4-trityloxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-acetamide (144588-13-6) + N-{9-((2R,3R,4R,5R)-4-Hydroxy-3-trityloxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-acetamide

Guidance literature:

With 2,4,6-trimethyl-pyridine; silver nitrate; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1021/jo00052a055

Reference yield: 20.0%

trityl chloride (76-83-5) + 2-N-Acetyl-6-O-((4-nitrophenyl)ethyl)guanosine → N-{9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-acetamide (144588-12-5) + N-{9-((2R,3R,4S,5R)-3-Hydroxy-4-trityloxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-acetamide (144588-13-6) + N-{9-((2R,3R,4R,5R)-4-Hydroxy-3-trityloxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-acetamide

Guidance literature:

With dmap; at 80 - 100 ℃; for 96h;

DOI:10.1021/jo00052a055

Reference yield:

trityl chloride (76-83-5) → N-{9-((2R,3R,4S,5R)-3-Hydroxy-4-trityloxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-acetamide (144588-13-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / 4-(dimethylamino)pyridine (DMAP) / 96 h / Ambient temperature

2: 40 percent / 2,4,6-collidine, AgNO₃ / dimethylformamide / Ambient temperature

With 2,4,6-trimethyl-pyridine; dmap; silver nitrate; In N,N-dimethyl-formamide;

DOI:10.1021/jo00052a055

upstream raw materials:

trityl chloride

N-{9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-acetamide