3-(tert-butyldimethylsilyloxy)-2-(5-hydroxypent-3-ynyl)-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate

Base Information

Chemical Name:3-(tert-butyldimethylsilyloxy)-2-(5-hydroxypent-3-ynyl)-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate
CAS No.:1418184-13-0
Molecular Formula:C₂₀H₃₃F₃O₅SSi
Molecular Weight:470.626
Hs Code.:

Synonyms:3-(tert-butyldimethylsilyloxy)-2-(5-hydroxypent-3-ynyl)-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate

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Chemical Property of 3-(tert-butyldimethylsilyloxy)-2-(5-hydroxypent-3-ynyl)-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate

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Technology Process of 3-(tert-butyldimethylsilyloxy)-2-(5-hydroxypent-3-ynyl)-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate

There total 3 articles about 3-(tert-butyldimethylsilyloxy)-2-(5-hydroxypent-3-ynyl)-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate 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: 65.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 1418184-12-9
3-(tert-butyldimethylsilyloxy)-2-(but-3-ynyl)-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate

: 1418184-13-0
3-(tert-butyldimethylsilyloxy)-2-(5-hydroxypent-3-ynyl)-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate

Guidance literature:: 3-(tert-butyldimethylsilyloxy)-2-(but-3-ynyl)-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate; With ethylmagnesium bromide; In tetrahydrofuran; at 0 - 50 ℃; for 2h; Inert atmosphere;

formaldehyd; In tetrahydrofuran; at 20 ℃; Inert atmosphere;
DOI:10.1016/j.tet.2012.12.014

Reference yield:

: 1418184-11-8
3-(tert-butyldimethylsilyloxy)-2-(3-hydroxypropyl)-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate

: 1418184-13-0
3-(tert-butyldimethylsilyloxy)-2-(5-hydroxypent-3-ynyl)-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3.5 h / 20 °C / Inert atmosphere

1.2: Ohira-Bestmann reagent / 20 °C / Inert atmosphere

2.1: ethylmagnesium bromide / tetrahydrofuran / 2 h / 0 - 50 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

With ethylmagnesium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide;
DOI:10.1016/j.tet.2012.12.014

Reference yield:

: 1131-02-8
2-allyl-5,5-dimethylcyclohexane-1,3-dione

: 1418184-13-0
3-(tert-butyldimethylsilyloxy)-2-(5-hydroxypent-3-ynyl)-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

1.2: 1 h / 20 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2.2: 1.5 h / 0 - 20 °C / Inert atmosphere

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3.5 h / 20 °C / Inert atmosphere

3.2: Ohira-Bestmann reagent / 20 °C / Inert atmosphere

4.1: ethylmagnesium bromide / tetrahydrofuran / 2 h / 0 - 50 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

With 1H-imidazole; ethylmagnesium bromide; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2012.12.014