N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-8-bromo-2'-deoxyadenosine

Base Information

• Chemical Name: N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-8-bromo-2'-deoxyadenosine
• CAS No.: 129451-79-2
• Molecular Formula: C38H34BrN5O6
• Molecular Weight: 736.622
• DSSTox Substance ID: DTXSID201142952
• Nikkaji Number: J1.478.127G
• Mol file: 129451-79-2.mol

Synonyms:SCHEMBL6710679;FFUDCIXZEUGJLO-DCMFLLSESA-N;DTXSID201142952;n6-benzoyl-8-bromo-5'-o-(4,4'-dimethoxytrityl)-2'-deoxyadenosine;N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-8-bromo-2'-deoxyadenosine;129451-79-2

Chemical Property of N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-8-bromo-2'-deoxyadenosine

Chemical Property:

• XLogP3: 5.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 735.16925
• Heavy Atom Count: 50
• Complexity: 1060

Purity/Quality:

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)OCC4C(CC(O4)N5C6=NC=NC(=C6N=C5Br)NC(=O)C7=CC=CC=C7)O
• Isomeric SMILES: COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)OC[C@@H]4[C@H](C[C@@H](O4)N5C6=NC=NC(=C6N=C5Br)NC(=O)C7=CC=CC=C7)O

Technology Process of N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-8-bromo-2'-deoxyadenosine

There total 9 articles about N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-8-bromo-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:

N-(9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-trimethylsilanyloxy-tetrahydro-furan-2-yl}-8-bromo-9H-purin-6-yl)-benzamide → N-(9-{5-[bis(4-methoxyphenyl)phenylmethoxyphenyl]-4-hydroxytetrahydrofuran-2-yl}-8-bromo-9H-purin-6-yl)benzamide (129451-79-2)

Guidance literature:

With ammonia; In methanol; at 5 ℃; for 1h;

DOI:10.1021/ol006303f

Reference yield:

8-bromo-2'-deoxyadenosine (14985-44-5,90968-89-1) → N-(9-{5-[bis(4-methoxyphenyl)phenylmethoxyphenyl]-4-hydroxytetrahydrofuran-2-yl}-8-bromo-9H-purin-6-yl)benzamide (129451-79-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 81 percent / DMAP / pyridine

2.1: pyridine / 1 h / -5 - 20 °C

2.2: pyridine

3.1: NH₃ / methanol / 1 h / 5 °C

With dmap; ammonia; In pyridine; methanol; 1.1: Substitution / 2.1: silylation / 2.2: Acylation / 3.1: desilylation;

DOI:10.1021/ol006303f

Reference yield:

5-(6-amino-8-bromo-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-ol (149540-21-6) → N-(9-{5-[bis(4-methoxyphenyl)phenylmethoxyphenyl]-4-hydroxytetrahydrofuran-2-yl}-8-bromo-9H-purin-6-yl)benzamide (129451-79-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine / 1 h / -5 - 20 °C

1.2: pyridine

2.1: NH₃ / methanol / 1 h / 5 °C

With ammonia; In pyridine; methanol; 1.1: silylation / 1.2: Acylation / 2.1: desilylation;

DOI:10.1021/ol006303f

upstream raw materials:

4,4'-dimethoxytrityl chloride

N-[8-Bromo-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide

8-bromo-2'-deoxyadenosine

5-(6-amino-8-bromo-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-ol

Downstream raw materials:

N⁶-benzoyl-5'-O-<4,4'-dimethoxytrityl-8-amino(2-aminoethyl)>-2'-deoxyadenosine

N⁶-benzoyl-5'-O-(4,4'-dimethoxytrityl)-8-[2-(imidazol-4-yl)ethylamino]-2'-deoxyadenosine

N-{9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-8-[3-(3-phenothiazin-10-yl-propionylamino)-prop-1-ynyl]-9H-purin-6-yl}-benzamide

9,10-Dioxo-9,10-dihydro-anthracene-2-carboxylic acid [3-(6-benzoylamino-9-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-9H-purin-8-yl)-prop-2-ynyl]-amide