(R)-6-[(E)-(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-oxo-6-phenyl-hex-5-enyl]-5,6-dihydro-pyran-2-one

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Chemical Name:(R)-6-[(E)-(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-oxo-6-phenyl-hex-5-enyl]-5,6-dihydro-pyran-2-one
CAS No.:406676-61-7
Molecular Formula:C₂₃H₃₂O₄Si
Molecular Weight:400.59
Hs Code.:

Synonyms:(R)-6-[(E)-(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-oxo-6-phenyl-hex-5-enyl]-5,6-dihydro-pyran-2-one

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Chemical Property of (R)-6-[(E)-(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-oxo-6-phenyl-hex-5-enyl]-5,6-dihydro-pyran-2-one

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Technology Process of (R)-6-[(E)-(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-oxo-6-phenyl-hex-5-enyl]-5,6-dihydro-pyran-2-one

There total 9 articles about (R)-6-[(E)-(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-oxo-6-phenyl-hex-5-enyl]-5,6-dihydro-pyran-2-one 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: 76.0%

: 406676-60-6
(R)-6-{(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-[2-((E)-styryl)-[1,3]dithian-2-yl]-propyl}-5,6-dihydro-pyran-2-one

: 406676-61-7
(R)-6-[(E)-(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-oxo-6-phenyl-hex-5-enyl]-5,6-dihydro-pyran-2-one

Guidance literature:: With mercury(I) perchlorate; calcium carbonate; In tetrahydrofuran; at 0 ℃; for 0.0833333h;
DOI:10.1016/S0957-4166(01)00506-7

Reference yield:

: 14371-10-9
(E)-3-phenylpropenal

: 406676-61-7
(R)-6-[(E)-(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-oxo-6-phenyl-hex-5-enyl]-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 70 percent / ceric ammonium nitrate / CHCl₃ / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.42 h / -78 °C

2.2: 58 percent / BF₃*Et₂O / tetrahydrofuran / 1 h

3.1: 81 percent / imidazole / CH₂Cl₂ / 20 °C

4.1: 95 percent / aq. CF₃COOH / CHCl₃ / 2 h / 0 °C

5.1: NaH / tetrahydrofuran / 0 °C

5.2: n-BuLi / tetrahydrofuran; hexane / -10 °C

5.3: 148 mg / tetrahydrofuran; hexane / 1 h / -50 °C

6.1: 92 percent / NaBH₄ / tetrahydrofuran / 1 h / -40 °C

7.1: 53 percent / p-toluenesulfonic acid / CH₂Cl₂ / 2 h / 20 °C

8.1: 91 percent / Et₃N; MsCl / CH₂Cl₂ / -40 - 20 °C

9.1: 76 percent / CaCO₃; aq. HgClO₄ / tetrahydrofuran / 0.08 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; mercury(I) perchlorate; ammonium cerium(IV) nitrate; sodium hydride; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; calcium carbonate; In tetrahydrofuran; hexane; dichloromethane; chloroform;
DOI:10.1016/S0957-4166(01)00506-7

Reference yield:

: 69178-10-5
2-styryl-1,3-dithiane

: 406676-61-7
(R)-6-[(E)-(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-oxo-6-phenyl-hex-5-enyl]-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.42 h / -78 °C

1.2: 58 percent / BF₃*Et₂O / tetrahydrofuran / 1 h

2.1: 81 percent / imidazole / CH₂Cl₂ / 20 °C

3.1: 95 percent / aq. CF₃COOH / CHCl₃ / 2 h / 0 °C

4.1: NaH / tetrahydrofuran / 0 °C

4.2: n-BuLi / tetrahydrofuran; hexane / -10 °C

4.3: 148 mg / tetrahydrofuran; hexane / 1 h / -50 °C

5.1: 92 percent / NaBH₄ / tetrahydrofuran / 1 h / -40 °C

6.1: 53 percent / p-toluenesulfonic acid / CH₂Cl₂ / 2 h / 20 °C

7.1: 91 percent / Et₃N; MsCl / CH₂Cl₂ / -40 - 20 °C

8.1: 76 percent / CaCO₃; aq. HgClO₄ / tetrahydrofuran / 0.08 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; mercury(I) perchlorate; sodium hydride; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; calcium carbonate; In tetrahydrofuran; hexane; dichloromethane; chloroform;
DOI:10.1016/S0957-4166(01)00506-7