Adenosine,N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-deoxy-

Base Information

• Chemical Name: Adenosine,N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-deoxy-
• CAS No.: 84138-86-3
• Molecular Formula: C38H35 N5 O6
• Molecular Weight: 657.726
• DSSTox Substance ID: DTXSID90693021
• Wikidata: Q82622050
• Mol file: 84138-86-3.mol

Synonyms:Adenosine,N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-deoxy-;DTXSID90693021;N-Benzoyl-3'-deoxy-5'-O-[(2,3-dimethoxyphenyl)(diphenyl)methyl]adenosine

Chemical Property of Adenosine,N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-deoxy-

Chemical Property:

• PSA: 129.85000
• LogP: 5.82590
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 657.25873385
• Heavy Atom Count: 49
• Complexity: 1030

Purity/Quality:

99.3% ^*data from raw suppliers

N6-Benzoyl-3'-deoxy-5'-O-DMT-adenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC(=C1OC)C(C2=CC=CC=C2)(C3=CC=CC=C3)OCC4CC(C(O4)N5C=NC6=C(N=CN=C65)NC(=O)C7=CC=CC=C7)O
• Isomeric SMILES: COC1=CC=CC(=C1OC)C(C2=CC=CC=C2)(C3=CC=CC=C3)OC[C@@H]4C[C@H]([C@@H](O4)N5C=NC6=C(N=CN=C65)NC(=O)C7=CC=CC=C7)O

Technology Process of Adenosine,N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-deoxy-

There total 8 articles about Adenosine,N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-deoxy- 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: 84.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + N-(9-((2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide (76902-49-3) → N-(9-((2R,3R,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-hydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide (84138-86-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; dmap; In pyridine; for 4h; Ambient temperature;

DOI:10.1021/jo00052a053

Reference yield: 69.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + cordycepin (73-03-0) + benzoyl chloride (98-88-4) → N-(9-((2R,3R,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-hydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide (84138-86-3)

Guidance literature:

4,4'-dimethoxytrityl chloride; cordycepin; With pyridine; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 20 ℃; for 3h;

benzoyl chloride; In pyridine;

DOI:10.1002/1522-2675(200208)85:8<2284::AID-HLCA2284>3.0.CO;2-E

Reference yield:

cordycepin (73-03-0) → N-(9-((2R,3R,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-hydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide (84138-86-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / pyridine / 2.5 h / 0 °C

2: 91 percent / 1.5 M aq. NaOH / methanol; tetrahydrofuran / 0.5 h / 0 °C

3: 84 percent / diisopropylethylamine / (dimethylamino)pyridine / pyridine / 4 h / Ambient temperature

With pyridine; sodium hydroxide; N-ethyl-N,N-diisopropylamine; dmap; In tetrahydrofuran; pyridine; methanol;

DOI:10.1021/jo00052a053

upstream raw materials:

4,4'-dimethoxytrityl chloride

N-(9-((2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide

cordycepin

benzoyl chloride

Downstream raw materials:

N⁶,O^2'-dibenzoyl-5'-(dimethoxytrityl)-3'-deoxyadenosine

N⁶-benzoyl-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)adenosine 2'-(2-cyanoethyl diisopropylphosphoramidite)

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