3'-azido-6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyadenosine

Base Information

• Chemical Name: 3'-azido-6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyadenosine
• CAS No.: 195375-60-1
• Molecular Formula: C₂₃H₃₀N₈O₃Si
• Molecular Weight: 494.629

Synonyms:3'-azido-6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyadenosine

Chemical Property of 3'-azido-6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyadenosine

Chemical Property:

Purity/Quality:

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Technology Process of 3'-azido-6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyadenosine

There total 7 articles about 3'-azido-6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-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: 81.0%

6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-3'-xylo-adenosine (195375-59-8) → 3'-azido-6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyadenosine (195375-60-1)

Guidance literature:

With sodium azide; 2-(diphenylphosphino)pyridine; di-isopropyl azodicarboxylate; In N,N-dimethyl-formamide; for 4h;

DOI:10.1021/jo8018889

Reference yield:

C24H33N5O6SSi → 3'-azido-6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyadenosine (195375-60-1)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 110 ℃; for 1.5h; Inert atmosphere;

DOI:10.3762/bjoc.11.8

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 3'-azido-6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyadenosine (195375-60-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / Et₃N, DMAP / pyridine / 16 h / Ambient temperature

2: 94 percent / 2 M NaOH / methanol; dioxane / 0.08 h / 0 °C

3: 18.8 g / LiN₃, PPh₃, DEAD / dimethylformamide / 6 h / Ambient temperature

With dmap; sodium hydroxide; lithium azide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; pyridine; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo970801t

upstream raw materials:

6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-3'-xylo-adenosine

tert-butyldimethylsilyl chloride

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

Benzoic acid (2R,3R,5R)-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

Downstream raw materials:

3'-azido-N₆-benzoyl-2',3'-dideoxyadenosine

N-{9-[(2R,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(trityl-amino)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide

N-benzoyl-2 ^{FontWeight=Bold FontSize=10} ',3'-dideoxy-3'-[(triphenylmethyl)amino]adenosine

3'-amino-6-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyadenosine

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