((1S,2R,3R,4S)-4-azido-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3-((tert-butyldimethylsilyloxy)methyl)cyclopentyloxy)(tert-butyl)dimethylsilane

Base Information

• Chemical Name: ((1S,2R,3R,4S)-4-azido-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3-((tert-butyldimethylsilyloxy)methyl)cyclopentyloxy)(tert-butyl)dimethylsilane
• CAS No.: 1431141-68-2
• Molecular Formula: C₂₆H₅₇N₃O₃Si₃
• Molecular Weight: 544.013

Synonyms:((1S,2R,3R,4S)-4-azido-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3-((tert-butyldimethylsilyloxy)methyl)cyclopentyloxy)(tert-butyl)dimethylsilane

Chemical Property of ((1S,2R,3R,4S)-4-azido-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3-((tert-butyldimethylsilyloxy)methyl)cyclopentyloxy)(tert-butyl)dimethylsilane

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1S,2R,3R,4S)-4-azido-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3-((tert-butyldimethylsilyloxy)methyl)cyclopentyloxy)(tert-butyl)dimethylsilane

There total 1 articles about ((1S,2R,3R,4S)-4-azido-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3-((tert-butyldimethylsilyloxy)methyl)cyclopentyloxy)(tert-butyl)dimethylsilane 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:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → ((1S,2R,3R,4S)-4-azido-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3-((tert-butyldimethylsilyloxy)methyl)cyclopentyloxy)(tert-butyl)dimethylsilane (1431141-68-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sulfuric acid / 24 h / 50 - 80 °C / Sealed tube

2.1: DBN / methanol / 12 h / 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere

3.2: 8 h / Inert atmosphere

4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

6.1: 1H-imidazole / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere

6.2: 12 h / Inert atmosphere

7.1: dimethylaluminum chloride / dichloromethane; hexane / 3 h / 20 °C / Inert atmosphere

8.1: pyridine / 24 h / 20 °C / Inert atmosphere

9.1: sodium azide / N,N-dimethyl-formamide / 150 °C / Microwave irradiation

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; sodium azide; sulfuric acid; DBN; dimethylaluminum chloride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2013.03.069

Reference yield:

((1S,2R,3R,4S)-4-azido-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3-((tert-butyldimethylsilyloxy)methyl)cyclopentyloxy)(tert-butyl)dimethylsilane (1431141-68-2) → (1S,2R,3R,4S)-2-(2-hydroxyethyl)-3-(hydroxymethyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)cyclopentanol (1431141-69-3)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(ll) sulfate pentahydrate / methanol / 8 h / 50 °C / Sealed tube

2: copper(l) iodide; sodium hydroxide / methanol; water / 50 °C

With copper(l) iodide; copper(ll) sulfate pentahydrate; sodium hydroxide; In methanol; water;

DOI:10.1016/j.tetlet.2013.03.069

Reference yield:

((1S,2R,3R,4S)-4-azido-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3-((tert-butyldimethylsilyloxy)methyl)cyclopentyloxy)(tert-butyl)dimethylsilane (1431141-68-2) → (1S,2R,3S,4R)-4-(tert-butyldimethylsilyloxy)-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3-((tert-butyldimethylsilyloxy)methyl)cyclopentyl4-methylbenzenesulfonate (1431141-72-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: copper(ll) sulfate pentahydrate / methanol / 8 h / 50 °C / Sealed tube

2.1: copper(l) iodide; sodium hydroxide / methanol; water / 50 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere

5.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

5.2: Inert atmosphere

6.1: pyridine / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; copper(l) iodide; lithium aluminium tetrahydride; copper(ll) sulfate pentahydrate; sodium hydroxide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2013.03.069

upstream raw materials:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

Downstream raw materials:

(1S,2R,3R,4S)-2-(2-hydroxyethyl)-3-(hydroxymethyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)cyclopentanol

(1S,2R,3S,4R)-4-(tert-butyldimethylsilyloxy)-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3-((tert-butyldimethylsilyloxy)methyl)cyclopentyl4-methylbenzenesulfonate

(1R,2S,3R,4R)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)cyclopentanol

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