5'-O-(4,4'-dimethoxytrityl)-N⁶⁴-benzoyldeoxyriboadenosin-3'-yl hydrogen-phosphonothioate, triethylammonium salt

Base Information

• Chemical Name: 5'-O-(4,4'-dimethoxytrityl)-N⁶⁴-benzoyldeoxyriboadenosin-3'-yl hydrogen-phosphonothioate, triethylammonium salt
• CAS No.: 126899-02-3
• Molecular Formula: C₆H₁₅N*C₃₈H₃₆N₅O₇PS
• Molecular Weight: 838.965
• Mol file: 126899-02-3.mol

Synonyms:

Chemical Property of 5'-O-(4,4'-dimethoxytrityl)-N⁶⁴-benzoyldeoxyriboadenosin-3'-yl hydrogen-phosphonothioate, triethylammonium salt

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(4,4'-dimethoxytrityl)-N⁶⁴-benzoyldeoxyriboadenosin-3'-yl hydrogen-phosphonothioate, triethylammonium salt

There total 3 articles about 5'-O-(4,4'-dimethoxytrityl)-N⁶⁴-benzoyldeoxyriboadenosin-3'-yl hydrogen-phosphonothioate, triethylammonium salt 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: 72.0%

N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine (64325-78-6) + triethylamine (121-44-8) + O-phenyl H-phosphonothioate (p-chlorobenzyl)thiouronium salt → 5'-O-(4,4'-dimethoxytrityl)-N64-benzoyldeoxyriboadenosin-3'-yl hydrogen-phosphonothioate, triethylammonium salt (126899-02-3,126899-10-3,307309-54-2)

Guidance literature:

With pyridine; tert-butylchlorodiphenylsilane; In toluene;

DOI:10.1002/ejoc.200400550

Reference yield:

Triethylammonium 6-N-benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)adenosine 3'-H-phosphonate (118352-75-3) → 5'-O-(4,4'-dimethoxytrityl)-N64-benzoyldeoxyriboadenosin-3'-yl hydrogen-phosphonothioate, triethylammonium salt (126899-02-3,126899-10-3,307309-54-2)

Guidance literature:

Multi-step reaction with 2 steps

1: diphenyl chlorophosphate; pyridine / CH₂Cl₂ / 0.08 h

2: 0.15 g / 1,1,1,3,3,3-hexamethyldisilathiane / CH₂Cl₂ / 0.08 h

With pyridine; hexamethyldisilathiane; chlorophosphoric acid diphenyl ester; In dichloromethane; 1: Substitution / 2: Substitution;

DOI:10.1021/jo000729q

Reference yield:

triethylammonium hypophosphite (117872-98-7) + N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine (64325-78-6) → 5'-O-(4,4'-dimethoxytrityl)-N64-benzoyldeoxyriboadenosin-3'-yl hydrogen-phosphonothioate, triethylammonium salt (126899-02-3,126899-10-3,307309-54-2)

Guidance literature:

With pivaloyl chloride; sulfur; Yield given. Multistep reaction; 1) pyridine, 0 deg C, 15 min, 2) 1h;

DOI:10.1021/jo00298a023

upstream raw materials:

triethylammonium hypophosphite

N₆-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine

triethylamine

Triethylammonium 6-N-benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)adenosine 3'-H-phosphonate