N6-Benzoyl-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine

Base Information

• Chemical Name: N6-Benzoyl-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine
• CAS No.: 140712-79-4
• Molecular Formula: C38H35 N5 O6
• Molecular Weight: 657.71
• DSSTox Substance ID: DTXSID20579723
• Nikkaji Number: J1.176.328F
• Wikidata: Q82470331
• Mol file: 140712-79-4.mol

Synonyms:140712-79-4;N6-Benzoyl-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine;Adenosine, N-benzoyl-3'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-;N-(9-((2R,4S,5R)-4-(Bis(4-methoxyphenyl)(phenyl)methoxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide;N-Benzoyl-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine;N-[9-[(2R,4S,5R)-4-[bis(4-methoxyphenyl)-phenylmethoxy]-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]benzamide;N-{9-[(2R,4S,5R)-4-[bis(4-methoxyphenyl)(phenyl)methoxy]-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-yl}benzamide;LFXBQKFIXWICJR-WIHCDAFUSA-N;SCHEMBL3827645;DTXSID20579723;MFCD04972282;AKOS030241487;AS-72741;BP-58690;A904151;N6-bezoyl-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine;N6-BENZOYL-3-O-(4,4-DIMETHOXYTRITYL)-2-DEOXYADENOSINE;N-Benzoyl-3'-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2'-deoxyadenosine;N6-BENZOYL-3/'-O-(4,4/'-DIMETHOXYTRITYL)-2/'-DEOXYADENOSINE

Chemical Property of N6-Benzoyl-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine

Chemical Property:

• PSA: 129.85000
• LogP: 5.82590
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 657.25873385
• Heavy Atom Count: 49
• Complexity: 1020

Purity/Quality:

97% ^*data from raw suppliers

N6-Benzoyl-3''-O-(4,4''-dimethoxytrityl)-2''-deoxyadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)OC4CC(OC4CO)N5C=NC6=C(N=CN=C65)NC(=O)C7=CC=CC=C7
• Isomeric SMILES: COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)O[C@H]4C[C@@H](O[C@@H]4CO)N5C=NC6=C(N=CN=C65)NC(=O)C7=CC=CC=C7
• Description: N-Benzoyl-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine is a novel nucleoside analog that is structurally related to the natural nucleotide adenosine. N-Benzoyl-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine is an activator of ribonucleotide reductase, which converts ribonucleosides to deoxyribonucleosides.
• Uses: N-Benzoyl-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine is used as pharmaceutical intermediate.

Technology Process of N6-Benzoyl-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine

There total 5 articles about N6-Benzoyl-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine 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: 98.0%

N6-benzoyl-5'-O-(tert-bityldimethylsilyl)-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine → 6-N-benzoyl-2'-deoxy-3'-O-dimethoxytrityladenosine (140712-79-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 8h;

Reference yield:

N6-benzoyl-2'-deoxyadenosine (4546-72-9) → 6-N-benzoyl-2'-deoxy-3'-O-dimethoxytrityladenosine (140712-79-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂

3: tetrabutylammonium fluoride / tetrahydrofuran

With pyridine; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane;

DOI:10.1081/NCN-200033912

Reference yield:

N-{9-[4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide → 6-N-benzoyl-2'-deoxy-3'-O-dimethoxytrityladenosine (140712-79-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1081/NCN-200033912

upstream raw materials:

N₆-benzoyl-2'-deoxyadenosine

6-N-benzoyl-5'-O-tert-butyldiphenylsilyl-2'-deoxy-N-6-benzoyladenosine

N⁶-benzoyl-5′-O-(tert-butyldimethylsilyl)-2′-deoxyadenosine

Downstream raw materials:

{(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-ylmethoxymethyl}-phosphonic acid monomethyl ester

N⁶-benzoyl-2'-deoxy-3'-O-(4,4'-dimethoxytrityl)adenosin-5'-yl 5'-O-(9-phenylxxanthen-9-yl)thymidin-3'-yl phosphorofluoridate

C₄₇H₅₇N₆O₇PSi