N-Benzoyl-2'-deoxyadenosine 3'-benzoate

Base Information

• Chemical Name: N-Benzoyl-2'-deoxyadenosine 3'-benzoate
• CAS No.: 51549-54-3
• Molecular Formula: C24H21 N5 O5
• Molecular Weight: 459.461
• Hs Code.: 29389090
• European Community (EC) Number: 257-272-0
• DSSTox Substance ID: DTXSID70965874
• Nikkaji Number: J261.755B
• Wikidata: Q82948193
• Mol file: 51549-54-3.mol

Synonyms:51549-54-3;N6,3'-O-Dibenzoyl-2'-deoxyadenosine;N-Benzoyl-2'-deoxyadenosine 3'-benzoate;EINECS 257-272-0;[(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] benzoate;(2R,3S,5R)-5-(6-Benzamido-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl benzoate;C24H21N5O5;SCHEMBL11683614;DTXSID70965874;C24-H21-N5-O5;Adenosine, N-benzoyl-2'-deoxy-, 3'-benzoate;(2R,3S,5R)-5-(6-benzamido-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-yl benzoate;(2R,3S,5R)-5-(6-Benzamido-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ylbenzoate;9-(3-O-Benzoyl-2-deoxypentofuranosyl)-6-{[hydroxy(phenyl)methylidene]amino}-9H-purine

Chemical Property of N-Benzoyl-2'-deoxyadenosine 3'-benzoate

Chemical Property:

• PSA: 128.46000
• LogP: 2.65700
• Storage Temp.: −20°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 459.15426879
• Heavy Atom Count: 34
• Complexity: 714

Purity/Quality:

97% ^*data from raw suppliers

N6,3'-O-Dibenzoyl-2'-deoxyadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)CO)OC(=O)C5=CC=CC=C5
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)CO)OC(=O)C5=CC=CC=C5

Technology Process of N-Benzoyl-2'-deoxyadenosine 3'-benzoate

There total 11 articles about N-Benzoyl-2'-deoxyadenosine 3'-benzoate 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: 100.0%

N-benzoyl-5'-O-(bis(4-methoxyphenyl)phenylmethyl)-2'-deoxyadenosine 3'-benzoate (93966-66-6) → 3'-O-benzoyl-6-N-benzoyl-2'-deoxyadenosine (51549-54-3)

Guidance literature:

With trifluoroacetic acid; In chloroform;

DOI:10.1016/S0960-894X(00)00210-9

Reference yield:

C30H35N5O5Si → 3'-O-benzoyl-6-N-benzoyl-2'-deoxyadenosine (51549-54-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 30 ℃; for 16h; Large scale;

Reference yield:

N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine (64325-78-6) → 3'-O-benzoyl-6-N-benzoyl-2'-deoxyadenosine (51549-54-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: 100 percent / TFA / CHCl₃

With pyridine; trifluoroacetic acid; In chloroform; 1: Acylation / 2: acidolysis;

DOI:10.1016/S0960-894X(00)00210-9

upstream raw materials:

N-benzoyl-5'-O-(bis(4-methoxyphenyl)phenylmethyl)-2'-deoxyadenosine 3'-benzoate

2'-deoxy-D-adenosine

benzoyl chloride

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

Downstream raw materials:

Benzoic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[(2-chloro-phenoxy)-(2-trityloxy-ethylamino)-phosphoryloxymethyl]-tetrahydro-furan-3-yl ester

N-benzoyl-5'-O-(bis(4-methoxyphenyl)phenylmethyl)-2'-deoxyadenosine 3'-benzoate

Benzoic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[{(2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yloxy}-(2-chloro-phenoxy)-phosphoryloxymethyl]-tetrahydro-furan-3-yl ester

Benzoic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(diisopropylamino-methoxy-phosphanyloxymethyl)-tetrahydro-furan-3-yl ester

Refernces

• 1、 -. "COMPOSITIONS AND METHODS FOR CHEMICAL CLEAVAGE AND DEPROTECTION OF SURFACE-BOUND OLIGONUCLEOTIDES". Paragraph 0235; 0238; 0239. . Retrieved 2019/12/01.
• 2、 Matsuzaki, Jun-ichi,Hotoda, Hitoshi,Sekine, Mitsuo,Hata, Tsujiaki,Higuchi, Shigesada,et al.. "SELF-COMPLEMENTARY TETRADEOXYRIBONUCLEOSIDE TRIPHOSPHATES. CONVENIENT CHEMICAL PREPARATION AND SPECTROSCOPIC STUDIES IN SOLUTION". . p. 501 - 514. Retrieved 2007/10/02.