(3aS,4S,6R,6aR)-6-[6-amino-2-(4-azidophenethylamino)-9H-purin-9-yl]-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide

Base Information

• Chemical Name: (3aS,4S,6R,6aR)-6-[6-amino-2-(4-azidophenethylamino)-9H-purin-9-yl]-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide
• CAS No.: 1433011-00-7
• Molecular Formula: C₂₃H₂₈N₁₀O₄
• Molecular Weight: 508.54
• Mol file: 1433011-00-7.mol

Synonyms:(3aS,4S,6R,6aR)-6-[6-amino-2-(4-azidophenethylamino)-9H-purin-9-yl]-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide

Chemical Property of (3aS,4S,6R,6aR)-6-[6-amino-2-(4-azidophenethylamino)-9H-purin-9-yl]-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4S,6R,6aR)-6-[6-amino-2-(4-azidophenethylamino)-9H-purin-9-yl]-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide

There total 5 articles about (3aS,4S,6R,6aR)-6-[6-amino-2-(4-azidophenethylamino)-9H-purin-9-yl]-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide 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: 49.0%

(3aS,4S,6R,6aR)-6-[6-amino-2-(4-bromophenethylamino)-9H-purin-9-yl]-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide (1365619-15-3) → (3aS,4S,6R,6aR)-6-[6-amino-2-(4-azidophenethylamino)-9H-purin-9-yl]-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide (1433011-00-7)

Guidance literature:

With copper(l) iodide; sodium azide; N,N'-diethylethylenediamine; sodium L-ascorbate; In ethanol; at 100 ℃; for 6h;

DOI:10.1002/ejoc.201201657

Reference yield:

4-Bromophenethylamine (73918-56-6) → (3aS,4S,6R,6aR)-6-[6-amino-2-(4-azidophenethylamino)-9H-purin-9-yl]-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide (1433011-00-7)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine / ethanol / 72 h / 130 °C

2: sodium L-ascorbate; N,N'-diethylethylenediamine; sodium azide; copper(l) iodide / ethanol / 6 h / 100 °C

With copper(l) iodide; sodium azide; N,N'-diethylethylenediamine; sodium L-ascorbate; N-ethyl-N,N-diisopropylamine; In ethanol;

DOI:10.1002/ejoc.201201657

Reference yield:

t-butyl 2-(4-bromophenyl)ethylcarbamate (120157-97-3) → (3aS,4S,6R,6aR)-6-[6-amino-2-(4-azidophenethylamino)-9H-purin-9-yl]-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide (1433011-00-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium L-ascorbate; N,N'-diethylethylenediamine; sodium azide; copper(l) iodide / water; ethanol / 4 h / 100 °C

2.1: trifluoroacetic acid / 3 h / 0 °C

2.2: 0.17 h

3.1: N-ethyl-N,N-diisopropylamine / ethanol / 72 h / 110 °C

With copper(l) iodide; sodium azide; N,N'-diethylethylenediamine; sodium L-ascorbate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In ethanol; water;

DOI:10.1002/ejoc.201201657

upstream raw materials:

t-butyl 2-(4-bromophenyl)ethylcarbamate

4-Bromophenethylamine

2-chloro-2',3'-O-isopropylideneadenosine-5'-N-ethylcarboxamide

(3aS,4S,6R,6aR)-6-[6-amino-2-(4-bromophenethylamino)-9H-purin-9-yl]-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide

Downstream raw materials:

(2S,3S,4R,5R)-5-[6-amino-2-(4-azidophenethylamino)-9H-purin-9-yl]-N-ethyl-3,4-dihydroxytetrahydrofuran-2-carboxamide