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

Base Information

Chemical Name:(1R,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-((tert-butyldimethylsilyloxy)methyl)cyclopentanol
CAS No.:1431141-66-0
Molecular Formula:C₂₆H₅₈O₄Si₃
Molecular Weight:519.001
Hs Code.:

Synonyms:(1R,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-((tert-butyldimethylsilyloxy)methyl)cyclopentanol

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Chemical Property of (1R,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-((tert-butyldimethylsilyloxy)methyl)cyclopentanol

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Technology Process of (1R,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-((tert-butyldimethylsilyloxy)methyl)cyclopentanol

There total 1 articles about (1R,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-((tert-butyldimethylsilyloxy)methyl)cyclopentanol 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:

: 26054-46-6
(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

: 1431141-66-0
(1R,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-((tert-butyldimethylsilyloxy)methyl)cyclopentanol

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; lithium aluminium tetrahydride; 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: 85.0%

: 1431141-66-0
(1R,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-((tert-butyldimethylsilyloxy)methyl)cyclopentanol

: 98-59-9
p-toluenesulfonyl chloride

: 1431141-67-1
(1R,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-((tert-butyldimethylsilyloxy)methyl)cyclopentyl-4-methylbenzenesulfonate

Guidance literature:: With pyridine; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1016/j.tetlet.2013.03.069

Reference yield:

: 1431141-66-0
(1R,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-((tert-butyldimethylsilyloxy)methyl)cyclopentanol

: 1431141-69-3
(1S,2R,3R,4S)-2-(2-hydroxyethyl)-3-(hydroxymethyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)cyclopentanol

Guidance literature:: Multi-step reaction with 4 steps

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

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

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

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

With pyridine; copper(l) iodide; sodium azide; copper(ll) sulfate pentahydrate; sodium hydroxide; In methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2013.03.069