((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(4-azidobutoxy)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl ((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)sulfamate

Base Information

• Chemical Name: ((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(4-azidobutoxy)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl ((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)sulfamate
• CAS No.: 1548502-95-9
• Molecular Formula: C₃₄H₅₂N₁₀O₉SSi
• Molecular Weight: 805
• Mol file: 1548502-95-9.mol

Synonyms:((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(4-azidobutoxy)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl ((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)sulfamate

Chemical Property of ((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(4-azidobutoxy)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl ((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)sulfamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(4-azidobutoxy)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl ((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)sulfamate

There total 4 articles about ((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(4-azidobutoxy)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl ((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)sulfamate 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: 67.0%

((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(4-azidobutoxy)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl sulfamate (1548502-93-7) + Boc-Phe-ONSu (3674-06-4) → ((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(4-azidobutoxy)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl ((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)sulfamate (1548502-95-9)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.bmcl.2013.12.082

Reference yield:

((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(4-azidobutoxy)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methanol (1548502-85-7) → ((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(4-azidobutoxy)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl ((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)sulfamate (1548502-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / mineral oil; 1,2-dimethoxyethane / 0.5 h / 0 °C / Inert atmosphere

1.2: 10 h / 0 - 20 °C / Inert atmosphere

2.1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

With sodium hydride; caesium carbonate; In 1,2-dimethoxyethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.bmcl.2013.12.082

Reference yield:

(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(4-azidobutoxy)-2-(hydroxymethyl)tetrahydrofuranol (1548502-83-5) → ((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(4-azidobutoxy)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl ((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)sulfamate (1548502-95-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 16 h / 0 - 20 °C

2.1: trifluoroacetic acid / tetrahydrofuran; water / 3 h / 0 °C / Inert atmosphere

3.1: sodium hydride / mineral oil; 1,2-dimethoxyethane / 0.5 h / 0 °C / Inert atmosphere

3.2: 10 h / 0 - 20 °C / Inert atmosphere

4.1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium hydride; caesium carbonate; trifluoroacetic acid; In tetrahydrofuran; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.bmcl.2013.12.082

upstream raw materials:

9-((2R,3R,4R,5R)-3-(4-azidobutoxy)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine

((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(4-azidobutoxy)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methanol

((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(4-azidobutoxy)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl sulfamate

Boc-Phe-ONSu

Downstream raw materials:

((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(4-aminobutoxy)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl ((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)sulfamate