Adenosine, N-benzoyl-3'-deoxy-, 2',5'-dibenzoate

Base Information

• Chemical Name: Adenosine, N-benzoyl-3'-deoxy-, 2',5'-dibenzoate
• CAS No.: 4395-38-4
• Molecular Formula: C31H25N5O6
• Molecular Weight: 563.569
• Mol file: 4395-38-4.mol

Synonyms:

Chemical Property of Adenosine, N-benzoyl-3'-deoxy-, 2',5'-dibenzoate

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Adenosine, N-benzoyl-3'-deoxy-, 2',5'-dibenzoate

There total 5 articles about Adenosine, N-benzoyl-3'-deoxy-, 2',5'-dibenzoate 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: 88.0%

cordycepin (73-03-0) + benzoyl chloride (98-88-4) → N6,2',5'-tribenzoyl-3'-deoxyadenosine (4395-38-4)

Guidance literature:

With pyridine; at 0 ℃; for 2.5h;

DOI:10.1021/jo00052a053

Reference yield:

methyl β-D-erythro-3-deoxy-pentofuranoside (4395-36-2) → N6,2',5'-tribenzoyl-3'-deoxyadenosine (4395-38-4)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 16 h / Ambient temperature

2: 1.) acetyl bromide, 30 percent hydrobromide / 1.) AcOH, 20 min, r.t.; 2.) toluene, xylene, reflux, 30 min

With Acetyl bromide; hydrogen bromide; In pyridine;

DOI:10.1016/0040-4020(84)85113-3

Reference yield:

methyl (2S,3S,4R,5R)-3,4-epoxy-5-methoxy-2,3,4,5-tetrahydrofuran-2-carboxylate (79515-11-0) → N6,2',5'-tribenzoyl-3'-deoxyadenosine (4395-38-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / LiAlH₄ / tetrahydrofuran / 16 h / Ambient temperature

2: pyridine / 16 h / Ambient temperature

3: 1.) acetyl bromide, 30 percent hydrobromide / 1.) AcOH, 20 min, r.t.; 2.) toluene, xylene, reflux, 30 min

With lithium aluminium tetrahydride; Acetyl bromide; hydrogen bromide; In tetrahydrofuran; pyridine;

DOI:10.1016/0040-4020(84)85113-3

upstream raw materials:

cordycepin

benzoyl chloride

methyl 3-deoxy-2,5-di-O-benzoyl-β-D-erythro-pentofuranoside

methyl β-D-erythro-3-deoxy-pentofuranoside

Downstream raw materials:

Benzoic acid (2R,3R,5S)-5-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-(2-cyano-ethoxy)-phosphanyloxymethyl]-2-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester

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

N⁶,O^2'-dibenzoyl-3'-deoxyadenosine

N-(9-((2R,3R,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-hydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide

Refernces

• 1、 Ohno, Masaji,Ito, Yukishige,Arita, Masafumi,Shibata, Tomoyuki,Adachi, Kunitomo,Sawai, Hiroaki. "SYNTHETIC STUDIES ON BIOLOGICALLY ACTIVE NATURAL PRODUCTS BY A CHEMICOENZYMATIC APPROACH. ENANTIOSELECTIVE SYNTHESIS OF C- AND N-NUCLEOSIDES, SHOWDOMYCIN, 6-AZAPSEUDOURIDINE AND CORDYCEPIN". . p. 145 - 152. Retrieved 2007/10/02.