N6-Benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxyadenosine

Base Information

• Chemical Name: N6-Benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxyadenosine
• CAS No.: 51549-39-4
• Molecular Formula: C23H31 N5 O4 Si
• Molecular Weight: 469.616
• European Community (EC) Number: 684-336-9
• Nikkaji Number: J2.679.027A
• Mol file: 51549-39-4.mol

Synonyms:N6-Benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxyadenosine;5'-O-TBDMS-Bz-dA;51549-39-4;N-(9-((2R,4S,5R)-5-(((tert-Butyldimethylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide;N-[9-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]purin-6-yl]benzamide;N-Benzoyl-5'-O-Tert-Butyldimethylsilyl-2'-Deoxyadenosine;N-(9-((2R,4S,5R)-5-((TERT-BUTYLDIMETHYLSILYLOXY)METHYL)-4-HYDROXYTETRAHYDROFURAN-2-YL)-9H-PURIN-6-YL)BENZAMIDE;SCHEMBL3822219;BJZZQJFYKQPUGO-RCCFBDPRSA-N;MFCD04972281;AKOS024424134;AC-32244;BP-58691;MS-28688;PD157765;HY-138595;CS-0159270;G13296;N6 -benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxyadenosine;N6-bezoyl-5'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine;N6-benzoyl-5'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine

Chemical Property of N6-Benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxyadenosine

Chemical Property:

• PSA: 111.39000
• LogP: 3.82180
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 469.21453102
• Heavy Atom Count: 33
• Complexity: 684

Purity/Quality:

97% ^*data from raw suppliers

N6-Benzoyl-5''-O-tert-butyldimethylsilyl-2''-deoxyadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCC1C(CC(O1)N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)O
• Isomeric SMILES: CC(C)(C)[Si](C)(C)OC[C@@H]1[C@H](C[C@@H](O1)N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)O
• Description: N-Benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxyadenosine is an anti-cancer drug that is used to inhibit the growth of cancer cells in vitro. It has been shown to induce apoptosis in human leukemia cells and may be a novel anticancer agent. N6-BENZOYL-5'-O-TERT-BUTYLDIMETHYLSILYL-2'-DEOXYADENOSINE has also been shown to have antiviral activity against HIV, herpes simplex virus type 2, hepatitis B virus, and influenza A virus.
• Uses: N-Benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxyadenosine is used as pharmaceutical intermediate.

Technology Process of N6-Benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxyadenosine

There total 8 articles about N6-Benzoyl-5'-O-tert-butyldimethylsilyl-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: 88.0%

tert-butyldimethylsilyl chloride (18162-48-6) + N6-benzoyl-2'-deoxyadenosine (4546-72-9) → N6-benzoyl-5′-O-(tert-butyldimethylsilyl)-2′-deoxyadenosine (51549-39-4)

Guidance literature:

With pyridine; for 4h;

DOI:10.1021/jo8018889

Reference yield: 61.0%

1H-imidazole (288-32-4) + tert-butyldimethylsilyl chloride (18162-48-6) + N6-benzoyl-2'-deoxyadenosine (4546-72-9) → N6-benzoyl-5′-O-(tert-butyldimethylsilyl)-2′-deoxyadenosine (51549-39-4)

Guidance literature:

With sodium chloride; In chloroform; N,N-dimethyl-formamide;

Reference yield:

N6-benzoyl-2'-deoxyadenosine (4546-72-9) → N6-benzoyl-5′-O-(tert-butyldimethylsilyl)-2′-deoxyadenosine (51549-39-4)

Guidance literature:

Multi-step reaction with 3 steps

1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1.) 22 deg C, 1 h, 2.) r.t., 87 h

2: NaHCO₃ / methanol

3: imidazole / dimethylformamide

With 1H-imidazole; N,O-bis-(trimethylsilyl)-acetamide; sodium hydrogencarbonate; In methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00111a009

upstream raw materials:

tert-butyldimethylsilyl chloride

N₆-benzoyl-2'-deoxyadenosine

1H-imidazole

2'-deoxy-D-adenosine

Downstream raw materials:

N⁶-benzoyl-3′-O-(methylthiomethyl)-5′-O-(tert-butyldimethylsilyl)-2′-deoxyadenosine

N₆-benzoyl-5'-(tert-butyldimethylsilyl)-3'-(methyl phosphonyl) 2'-deoxyadenosine triethylammonium salt

N₆-benzoyl-5'-(tert-butyldimethylsilyl)-3'-(1-(benzyloxycarbonylamino)ethyl phosphonyl)-2'-deoxyadenosine triethylammonium salt