(1S,3R,5S)-5-tert-butyl(dimethyl)silyloxy-2,2-dimethyl-3-[(3'S)-3'-hydroxy-3'methylpent-4'-en-1'-yl]-4-methylenecyclohexyl acetate

Base Information

Chemical Name:(1S,3R,5S)-5-tert-butyl(dimethyl)silyloxy-2,2-dimethyl-3-[(3'S)-3'-hydroxy-3'methylpent-4'-en-1'-yl]-4-methylenecyclohexyl acetate
CAS No.:564476-58-0
Molecular Formula:C₂₃H₄₂O₄Si
Molecular Weight:410.67
Hs Code.:

Synonyms:(1S,3R,5S)-5-tert-butyl(dimethyl)silyloxy-2,2-dimethyl-3-[(3'S)-3'-hydroxy-3'methylpent-4'-en-1'-yl]-4-methylenecyclohexyl acetate

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Chemical Property of (1S,3R,5S)-5-tert-butyl(dimethyl)silyloxy-2,2-dimethyl-3-[(3'S)-3'-hydroxy-3'methylpent-4'-en-1'-yl]-4-methylenecyclohexyl acetate

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Technology Process of (1S,3R,5S)-5-tert-butyl(dimethyl)silyloxy-2,2-dimethyl-3-[(3'S)-3'-hydroxy-3'methylpent-4'-en-1'-yl]-4-methylenecyclohexyl acetate

There total 11 articles about (1S,3R,5S)-5-tert-butyl(dimethyl)silyloxy-2,2-dimethyl-3-[(3'S)-3'-hydroxy-3'methylpent-4'-en-1'-yl]-4-methylenecyclohexyl acetate 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:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 564476-58-0
(1S,3R,5S)-5-tert-butyl(dimethyl)silyloxy-2,2-dimethyl-3-[(3'S)-3'-hydroxy-3'methylpent-4'-en-1'-yl]-4-methylenecyclohexyl acetate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 78 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: 95 percent / i-Bu₂AlH / toluene / -70 °C

3.1: Ba(OH)2*8H₂O / tetrahydrofuran / 0.5 h / 20 °C

3.2: 598 mg / tetrahydrofuran; H₂O / 24 h / 20 °C

4.1: 89 percent / pyridine*p-TsOH / toluene / 7 h / 110 °C

5.1: 83 percent / Bu₃SnH; ZnCl₂; Pd(PPh₃)4 / tetrahydrofuran / 0.75 h / 20 °C

6.1: 138 mg / tetrahydrofuran / -20 - 0 °C

With 1H-imidazole; barium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; zinc(II) chloride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo034424y

Reference yield:

: 358339-06-7
(1R,5S)-(+)-8,8-dimethyl-2-methylene-6-oxabicyclo[3.2.1]octan-7-one

: 564476-58-0
(1S,3R,5S)-5-tert-butyl(dimethyl)silyloxy-2,2-dimethyl-3-[(3'S)-3'-hydroxy-3'methylpent-4'-en-1'-yl]-4-methylenecyclohexyl acetate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 86 percent / SeO₂; t-BuOOH; salicylic acid / CH₂Cl₂; H₂O / 72 h / Heating

2.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

3.1: 85 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.25 h / -18 °C

4.1: 78 percent / imidazole / dimethylformamide / 12 h / 20 °C

5.1: 95 percent / i-Bu₂AlH / toluene / -70 °C

6.1: Ba(OH)2*8H₂O / tetrahydrofuran / 0.5 h / 20 °C

6.2: 598 mg / tetrahydrofuran; H₂O / 24 h / 20 °C

7.1: 89 percent / pyridine*p-TsOH / toluene / 7 h / 110 °C

8.1: 83 percent / Bu₃SnH; ZnCl₂; Pd(PPh₃)4 / tetrahydrofuran / 0.75 h / 20 °C

9.1: 138 mg / tetrahydrofuran / -20 - 0 °C

With 1H-imidazole; tert.-butylhydroperoxide; barium dihydroxide; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; selenium(IV) oxide; cerium(III) chloride; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; salicylic acid; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2.1: Dess-Martin oxidation;
DOI:10.1021/jo034424y

Reference yield:

: 564476-63-7
(1S,3S,5S)-3-Hydroxy-8,8-dimethyl-2-methylene-6-oxa-bicyclo[3.2.1]octan-7-one

: 564476-58-0
(1S,3R,5S)-5-tert-butyl(dimethyl)silyloxy-2,2-dimethyl-3-[(3'S)-3'-hydroxy-3'methylpent-4'-en-1'-yl]-4-methylenecyclohexyl acetate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 78 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: 95 percent / i-Bu₂AlH / toluene / -70 °C

3.1: Ba(OH)2*8H₂O / tetrahydrofuran / 0.5 h / 20 °C

3.2: 598 mg / tetrahydrofuran; H₂O / 24 h / 20 °C

4.1: 89 percent / pyridine*p-TsOH / toluene / 7 h / 110 °C

5.1: 83 percent / Bu₃SnH; ZnCl₂; Pd(PPh₃)4 / tetrahydrofuran / 0.75 h / 20 °C

6.1: 138 mg / tetrahydrofuran / -20 - 0 °C

With 1H-imidazole; barium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; zinc(II) chloride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo034424y