3'-AZIDO-N6-BENZOYL-2',3'-DIDEOXYADENOSINE

Base Information

• Chemical Name: 3'-AZIDO-N6-BENZOYL-2',3'-DIDEOXYADENOSINE
• CAS No.: 869354-89-2
• Molecular Formula: C17H16N8O3
• Molecular Weight: 380.36
• Mol file: 869354-89-2.mol

Synonyms:3'-AZIDO-N6-BENZOYL-2',3'-DIDEOXYADENOSINE;N4-BENZOYL-3'-AZIDO-2',3'-DIDEOXYADENOSINE;N6-Benzoyl-3'-azido-2',3'-dideoxyadenosine;N6-Bz-3'-Azido-ddA

Chemical Property of 3'-AZIDO-N6-BENZOYL-2',3'-DIDEOXYADENOSINE

Chemical Property:

• PSA: 151.91000
• LogP: 1.56306

Purity/Quality:

98% ^*data from raw suppliers

3'-AZIDO-N6-BENZOYL-2',3'-DIDEOXYADENOSINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3'-AZIDO-N6-BENZOYL-2',3'-DIDEOXYADENOSINE

There total 5 articles about 3'-AZIDO-N6-BENZOYL-2',3'-DIDEOXYADENOSINE 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: 92.0%

3'-azido-6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyadenosine (195375-60-1) → 3'-azido-N6-benzoyl-2',3'-dideoxyadenosine (869354-89-2)

Guidance literature:

With Trimethylmethoxysilane; tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2.5h;

DOI:10.1021/jo8018889

Reference yield:

N6-benzoyl-5'-O-benzoyl-2'-deoxyadenosine (104769-16-6) → 3'-azido-N6-benzoyl-2',3'-dideoxyadenosine (869354-89-2)

Guidance literature:

Multi-step reaction with 3 steps

1: (CF₃SO₂)2O, pyridine / CH₂Cl₂

2: NaHCO₃ / methanol

3: 1.) (CF₃SO₂)2O, LiN₃, pyridine, 2.) aq. NH₃

With pyridine; ammonium hydroxide; lithium azide; trifluoromethylsulfonic anhydride; sodium hydrogencarbonate; In methanol; dichloromethane;

Reference yield:

N6-benzoyl-9-(3-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)adenine (116597-14-9) → 3'-azido-N6-benzoyl-2',3'-dideoxyadenosine (869354-89-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaHCO₃ / methanol

2: 1.) (CF₃SO₂)2O, LiN₃, pyridine, 2.) aq. NH₃

With pyridine; ammonium hydroxide; lithium azide; trifluoromethylsulfonic anhydride; sodium hydrogencarbonate; In methanol;

upstream raw materials:

N6-Benzoyl-9-(5-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)adenine

N⁶-benzoyl-5'-O-benzoyl-2'-deoxyadenosine

N⁶-benzoyl-9-(3-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)adenine

2'-deoxy-D-adenosine

Downstream raw materials:

N-[9-[(2R,4S,5S)-4-azido-5-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]tetrahydrofuran-2-yl]-9H-purin-6-yl]benzamide

3'-azido-N₆-benzoyl-2',3'-dideoxyadenosine-5'-O-(dibenzyl phosphate)

Refernces

• 1、 Wojczcwski,Faulstich,Engels. "Synthesis and application of 3′-amino-dye-terminators for dna sequencing". . p. 751 - 754. Retrieved 2007/10/03.