Adenosine, N-benzoyl-2'-deoxy-5'-O-[(4-methoxyphenyl)diphenylmethyl]-

Base Information

• Chemical Name: Adenosine, N-benzoyl-2'-deoxy-5'-O-[(4-methoxyphenyl)diphenylmethyl]-
• CAS No.: 24816-13-5
• Molecular Formula: C37H33N5O5
• Molecular Weight: 627.7
• Mol file: 24816-13-5.mol

Synonyms:6-N-benzoyl-5'-O-(monomethoxytrityl)-2'-deoxyadenosine;N-(9-{(2R,4S,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide;5'-O-(Methoxytrityl)-N6-benzoyldeoxyadenosine;N6-benzoyl-5'-O-monomethoxytrityl-2'-deoxyadenosine;N6-benzoyl-O5'-(4-methoxy-trityl)-2'-deoxy-adenosine;5'-O-monomethoxytrityl-N6-benzoyldeoxyadenosine;

Chemical Property of Adenosine, N-benzoyl-2'-deoxy-5'-O-[(4-methoxyphenyl)diphenylmethyl]-

Chemical Property:

• PSA: 120.62000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 5.81730

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Adenosine, N-benzoyl-2'-deoxy-5'-O-[(4-methoxyphenyl)diphenylmethyl]-

There total 7 articles about Adenosine, N-benzoyl-2'-deoxy-5'-O-[(4-methoxyphenyl)diphenylmethyl]- 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: 48.0%

4-methoxytriphenylmethyl trifluoroacetate (90173-59-4) + N6-benzoyl-2'-deoxyadenosine (4546-72-9) → 6-N-Benzoyl-5'-O-(4-methoxyphenyl)diphenylmethyl-2'-desoxyadenosin (24816-13-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.tetlet.2016.07.062

Reference yield:

N6-benzoyl-2'-deoxyadenosine (4546-72-9) + mono-4-methoxytrityl chloride (14470-28-1) → 6-N-Benzoyl-5'-O-(4-methoxyphenyl)diphenylmethyl-2'-desoxyadenosin (24816-13-5)

Guidance literature:

With pyridine; at 25 ℃; for 3h;

DOI:10.1248/cpb.29.3274

Reference yield:

p-methoxytrityl alcohol (847-83-6) → 6-N-Benzoyl-5'-O-(4-methoxyphenyl)diphenylmethyl-2'-desoxyadenosin (24816-13-5)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane / 2 h / 20 °C / Inert atmosphere; Schlenk technique

2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2016.07.062

upstream raw materials:

N⁶-Benzoyl-2'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)adenosine

N₆-benzoyl-2'-deoxyadenosine

mono-4-methoxytrityl chloride

benzoyl chloride

Downstream raw materials:

Phosphoric acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 4-chloro-phenyl ester

N⁶-benzoyl-5'-O-monomethoxytrityl-2'-deoxyadenosine 3'(bis<2-(p-nitrophenyl)ethyl> phosphate)

Phosphoric acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester; compound with pyridine

5'-O-(Methoxytrityl)-N⁶-benzoyldeoxyadenosine 3'-<2-cyanoethyl S-(dimethylthiocarbamoyl)thiophosphate>