(4R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4-hydroxy-cyclohex-2-enone

Base Information

Chemical Name:(4R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4-hydroxy-cyclohex-2-enone
CAS No.:903522-46-3
Molecular Formula:C₂₉H₅₄O₃Si
Molecular Weight:478.831
Hs Code.:

Synonyms:(4R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4-hydroxy-cyclohex-2-enone

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Chemical Property of (4R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4-hydroxy-cyclohex-2-enone

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Technology Process of (4R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4-hydroxy-cyclohex-2-enone

There total 9 articles about (4R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4-hydroxy-cyclohex-2-enone 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:

: Acetic acid (1R,2R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-2-((Z)-heptadec-10-enyl)-2-hydroxy-5-oxo-cyclohexyl ester

: 903522-46-3
(4R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4-hydroxy-cyclohex-2-enone

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃;
DOI:10.1021/ol061000s

Reference yield:

: 903522-42-9
(3S,4aR,8aR)-8a-((Z)-Heptadec-10-enyl)-3-methyl-4a,8a-dihydro-5H-benzo[1,4]dioxine-2,6-dione

: 903522-46-3
(4R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4-hydroxy-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 8 steps

1.1: RhCl(PPh₃)3 / benzene / 2 h

1.2: 84 percent / dimethyldioxirane / CH₂Cl₂ / 1 h / 0 °C

2.1: 66 percent / DMAP / dimethylformamide / 20 °C

3.1: Dibal-H / tetrahydrofuran / 0.5 h / -78 °C

4.1: 51.1 mg / TFA / CH₂Cl₂ / 20 °C

5.1: 78 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves; TPAP / CH₂Cl₂ / 1 h / 20 °C

6.1: 50 percent / TMSCl / CH₂Cl₂ / 4 h

7.1: pyridine; DMAP / ethyl acetate

8.1: 1.9 mg / DBU / CH₂Cl₂ / 20 °C

With pyridine; dmap; chloro-trimethyl-silane; tetrapropylammonium perruthennate; 4 A molecular sieve; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; RhCl(PPh₃)3; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ol061000s

Reference yield:

: 903522-51-0
(3S,4aS,8aR)-5-Bromo-8a-((Z)-heptadec-10-enyl)-3-methyl-4a,8a-dihydro-5H-benzo[1,4]dioxine-2,6-dione

: 903522-46-3
(4R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4-hydroxy-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 9 steps

1.1: 85 percent / NaI; TMSI / acetonitrile / 4 h

2.1: RhCl(PPh₃)3 / benzene / 2 h

2.2: 84 percent / dimethyldioxirane / CH₂Cl₂ / 1 h / 0 °C

3.1: 66 percent / DMAP / dimethylformamide / 20 °C

4.1: Dibal-H / tetrahydrofuran / 0.5 h / -78 °C

5.1: 51.1 mg / TFA / CH₂Cl₂ / 20 °C

6.1: 78 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves; TPAP / CH₂Cl₂ / 1 h / 20 °C

7.1: 50 percent / TMSCl / CH₂Cl₂ / 4 h

8.1: pyridine; DMAP / ethyl acetate

9.1: 1.9 mg / DBU / CH₂Cl₂ / 20 °C

With pyridine; dmap; chloro-trimethyl-silane; tetrapropylammonium perruthennate; trimethylsilyl iodide; 4 A molecular sieve; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; sodium iodide; RhCl(PPh₃)3; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/ol061000s