(3R,5S)-5-(tert-butyldimethylsilyloxy)-5-(oxiran-2-yl)pent-1-yn-3-yl benzoate

Base Information

Chemical Name:(3R,5S)-5-(tert-butyldimethylsilyloxy)-5-(oxiran-2-yl)pent-1-yn-3-yl benzoate
CAS No.:1435752-11-6
Molecular Formula:C₂₀H₂₈O₄Si
Molecular Weight:360.525
Hs Code.:

Synonyms:(3R,5S)-5-(tert-butyldimethylsilyloxy)-5-(oxiran-2-yl)pent-1-yn-3-yl benzoate

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Chemical Property of (3R,5S)-5-(tert-butyldimethylsilyloxy)-5-(oxiran-2-yl)pent-1-yn-3-yl benzoate

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Technology Process of (3R,5S)-5-(tert-butyldimethylsilyloxy)-5-(oxiran-2-yl)pent-1-yn-3-yl benzoate

There total 6 articles about (3R,5S)-5-(tert-butyldimethylsilyloxy)-5-(oxiran-2-yl)pent-1-yn-3-yl benzoate 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%

: 1435751-83-9
(3R,5S)-5-hydroxy-5-(oxiran-2-yl)pent-1-yn-3-yl benzoate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1435752-11-6
(3R,5S)-5-(tert-butyldimethylsilyloxy)-5-(oxiran-2-yl)pent-1-yn-3-yl benzoate

Guidance literature:: With 1H-imidazole; In tetrahydrofuran; at 0 - 30 ℃; for 24h; Inert atmosphere;
DOI:10.1021/jo400607v

Reference yield:

: C₃₀H₄₉BO₂Si

: 1435752-11-6
(3R,5S)-5-(tert-butyldimethylsilyloxy)-5-(oxiran-2-yl)pent-1-yn-3-yl benzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: lithium borohydride / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 0.83 h / 0 - 20 °C / Inert atmosphere

2.1: potassium carbonate / methanol / 1 h / 20 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 15 h / 0 - 20 °C / Inert atmosphere

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 15 h / 20 °C / Inert atmosphere

5.1: 1H-imidazole / tetrahydrofuran / 24 h / 0 - 30 °C / Inert atmosphere

With 1H-imidazole; lithium borohydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/jo400607v

Reference yield:

: 1435751-58-8
(3R,5S)-5-hydroxyhept-6-en-1-yn-3-yl benzoate

: 1435752-11-6
(3R,5S)-5-(tert-butyldimethylsilyloxy)-5-(oxiran-2-yl)pent-1-yn-3-yl benzoate

Guidance literature:: Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 15 h / 20 °C / Inert atmosphere

2: 1H-imidazole / tetrahydrofuran / 24 h / 0 - 30 °C / Inert atmosphere

With 1H-imidazole; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo400607v