(+)-(5S)-1-[5-(tert-butyldimethylsilyloxy)-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]-cyclobutanol

Base Information

Chemical Name:(+)-(5S)-1-[5-(tert-butyldimethylsilyloxy)-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]-cyclobutanol
CAS No.:353248-31-4
Molecular Formula:C₂₂H₃₅NO₄SSi
Molecular Weight:437.676
Hs Code.:

Synonyms:(+)-(5S)-1-[5-(tert-butyldimethylsilyloxy)-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]-cyclobutanol

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Chemical Property of (+)-(5S)-1-[5-(tert-butyldimethylsilyloxy)-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]-cyclobutanol

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Technology Process of (+)-(5S)-1-[5-(tert-butyldimethylsilyloxy)-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]-cyclobutanol

There total 5 articles about (+)-(5S)-1-[5-(tert-butyldimethylsilyloxy)-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]-cyclobutanol 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:

: 1191-95-3
cyclobutanone

: (+)-(3S)-3-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-6-trimethylstannyl-1,2,3,4-tetrahydropyridine

: 353248-31-4
(+)-(5S)-1-[5-(tert-butyldimethylsilyloxy)-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]-cyclobutanol

Guidance literature:: (+)-(3S)-3-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-6-trimethylstannyl-1,2,3,4-tetrahydropyridine; With methyllithium; magnesium bromide; In diethyl ether;

cyclobutanone; In diethyl ether; at -100 ℃; Further stages.;
DOI:10.1021/ol0160708

Reference yield:

: 24211-54-9
(S)-5-hydroxypiperidin-2-one

: 353248-31-4
(+)-(5S)-1-[5-(tert-butyldimethylsilyloxy)-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]-cyclobutanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 90 percent / imidazole / dimethylformamide / 13 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 75 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C

3.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / -78 °C

3.2: 76 percent / tetrahydrofuran; toluene / -78 - 20 °C

With 1H-imidazole; n-butyllithium; potassium hexamethylsilazane; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo0493572

Reference yield:

: 87179-81-5
(-)-(5S)-5-(tert-butyldimethylsilanyloxy)piperidin-2-one

: 353248-31-4
(+)-(5S)-1-[5-(tert-butyldimethylsilyloxy)-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]-cyclobutanol

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 75 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C

2.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / -78 °C

2.2: 76 percent / tetrahydrofuran; toluene / -78 - 20 °C

With n-butyllithium; potassium hexamethylsilazane; In tetrahydrofuran; hexane; toluene;
DOI:10.1021/jo0493572