N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-(2-methoxyethyl)adenosine

Base Information

• Chemical Name: N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-(2-methoxyethyl)adenosine
• CAS No.: 251647-48-0
• Molecular Formula: C₄₁H₄₁N₅O₈
• Molecular Weight: 731.805
• Mol file: 251647-48-0.mol

Synonyms:N-Benzoyl-5'-O-DMTr-2'-O-(2-methoxyethyl)adenosine;

Chemical Property of N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-(2-methoxyethyl)adenosine

Chemical Property:

• PKA: 7.87±0.43(Predicted)
• PSA: 151.80000
• Density: 1.31
• LogP: 5.77840
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Sparingly), Chloroform (Slightly), DMF (Slightly, Sonicated), DMSP

Purity/Quality:

98%, ^*data from raw suppliers

N-(9-((2R,3R,4R,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxy-3-(2-methoxyethoxy)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Benzoyl-5''-O-[bis(4-methoxyphenyl)phenylmethyl]-2''-O-(2-methoxyethyl)-adenosine is a commonly used reactant in the preparation of nucleosidic phosphoramidite derivatives.

Technology Process of N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-(2-methoxyethyl)adenosine

There total 6 articles about N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-(2-methoxyethyl)adenosine 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: 86.1%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-O-methoxyethyl- N6-benzoyl -adenosine (333335-93-6) → 5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-N6-benzoyladenosine (251647-48-0)

Guidance literature:

2'-O-methoxyethyl- N⁶-benzoyl -adenosine; With pyridine; at 20 ℃; for 0.5h; Inert atmosphere;

4,4'-dimethoxytrityl chloride; for 4h;

Reference yield: 30.0%

4,4'-dimethoxytrityl alcohol (40615-35-8) + 2'-O-methoxyethyl- N6-benzoyl -adenosine (333335-93-6) → 5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-N6-benzoyladenosine (251647-48-0)

Guidance literature:

With copper(II) nitrate; In dichloromethane; for 6h; Reagent/catalyst; Reflux;

DOI:10.1080/15257770.2018.1460480

Reference yield:

adenosine (58-61-7) → 5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-N6-benzoyladenosine (251647-48-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 9 h / 20 °C / Cooling with ice; Inert atmosphere

2.1: pyridine; chloro-trimethyl-silane / 1.33 h / Inert atmosphere; Cooling with ice

2.2: 2 h

3.1: pyridine / 0.5 h / 20 °C / Inert atmosphere

3.2: 4 h

With pyridine; chloro-trimethyl-silane; sodium hydride; In N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

4,4'-dimethoxytrityl chloride

2'-O-methoxyethyl- N⁶-benzoyl -adenosine

adenosine

2'-O-(2-methoxyethyl)adenosine

Refernces

• 1、 Li,Lightfoot,Halloy,Malinowska,Berk,Behera,Schümperli,Hall. "Synthesis and cellular activity of stereochemically-pure 2′-O-(2-methoxyethyl)-phosphorothioate oligonucleotides". supporting information. p. 541 - 544. Retrieved 2017/01/13.