(1S,2S,3R)-2-{(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-3-[(4S,5S)-4-methyl-5-(3-methyl-but-3-enyl)-cyclopent-1-enyl]-but-2-enyl}-3-isopropyl-1-methyl-cyclopentanecarbaldehyde

Base Information

Chemical Name:(1S,2S,3R)-2-{(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-3-[(4S,5S)-4-methyl-5-(3-methyl-but-3-enyl)-cyclopent-1-enyl]-but-2-enyl}-3-isopropyl-1-methyl-cyclopentanecarbaldehyde
CAS No.:896104-64-6
Molecular Formula:C₄₁H₅₈O₂Si
Molecular Weight:610.996
Hs Code.:

(1S,2S,3R)-2-{(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-3-[(4S,5S)-4-methyl-5-(3-methyl-but-3-enyl)-cyclopent-1-enyl]-but-2-enyl}-3-isopropyl-1-methyl-cyclopentanecarbaldehyde

Synonyms:(1S,2S,3R)-2-{(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-3-[(4S,5S)-4-methyl-5-(3-methyl-but-3-enyl)-cyclopent-1-enyl]-but-2-enyl}-3-isopropyl-1-methyl-cyclopentanecarbaldehyde

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Chemical Property of (1S,2S,3R)-2-{(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-3-[(4S,5S)-4-methyl-5-(3-methyl-but-3-enyl)-cyclopent-1-enyl]-but-2-enyl}-3-isopropyl-1-methyl-cyclopentanecarbaldehyde

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Technology Process of (1S,2S,3R)-2-{(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-3-[(4S,5S)-4-methyl-5-(3-methyl-but-3-enyl)-cyclopent-1-enyl]-but-2-enyl}-3-isopropyl-1-methyl-cyclopentanecarbaldehyde

There total 24 articles about (1S,2S,3R)-2-{(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-3-[(4S,5S)-4-methyl-5-(3-methyl-but-3-enyl)-cyclopent-1-enyl]-but-2-enyl}-3-isopropyl-1-methyl-cyclopentanecarbaldehyde 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: 35.0%

: 896104-62-4
(1S,2S,3R)-2-{(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-3-[(4S,5S)-5-((E)-4-iodo-3-methyl-but-3-enyl)-4-methyl-cyclopent-1-enyl]-but-2-enyl}-3-isopropyl-1-methyl-cyclopentanecarbaldehyde

: 896104-64-6
(1S,2S,3R)-2-{(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-3-[(4S,5S)-4-methyl-5-(3-methyl-but-3-enyl)-cyclopent-1-enyl]-but-2-enyl}-3-isopropyl-1-methyl-cyclopentanecarbaldehyde

: 896104-63-5
(2Z,11E)-(5S,6R,9S,10R,15S,16S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-isopropyl-9,12,16-trimethyl-tricyclo[13.3.0.0^5,9]octadeca-1⁽¹⁸⁾,2,11-trien-10-ol

: 896429-17-7
(2Z,11E)-(5S,6R,9S,10S,15S,16S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-isopropyl-9,12,16-trimethyl-tricyclo[13.3.0.0^5,9]octadeca-1⁽¹⁸⁾,2,11-trien-10-ol

Guidance literature:: With chromium dichloride; nickel dichloride; In tetrahydrofuran; dimethyl sulfoxide; for 42h;
DOI:10.1021/jo0604585

Reference yield:

: 896104-51-1
(E)-(2S,3S)-2-[3-(4-Methoxy-benzyloxy)-propyl]-3-methyl-hex-4-enoic acid

: 896104-64-6
(1S,2S,3R)-2-{(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-3-[(4S,5S)-4-methyl-5-(3-methyl-but-3-enyl)-cyclopent-1-enyl]-but-2-enyl}-3-isopropyl-1-methyl-cyclopentanecarbaldehyde

Guidance literature:: Multi-step reaction with 15 steps

1.1: 80 percent / MsCl; Et₃N / tetrahydrofuran / 1 h / 0 °C

2.1: 82 percent / tetrahydrofuran / 20 °C

3.1: Grubbs catalyst / CH₂Cl₂ / Heating

4.1: H₂ / Pd/C / ethyl acetate / 2 h

5.1: LHMDS / toluene / 1 h / -78 °C

5.2: tetrahydrofuran / 4 h / -78 - 20 °C

6.1: HSnBu₃; Pd(PPh₃)4 / tetrahydrofuran / 2 h

6.2: 1.18 percent / Pd(PPh₃)4; LiCl; CuCl / dimethylsulfoxide / 37 h / 60 °C

7.1: 87 percent / DIBAL-H / CH₂Cl₂ / -78 - 20 °C

8.1: 93 percent / imidazole / dimethylformamide / 18 h / 20 °C

9.1: 91 percent / catecholborane bromide; 2,6-lutidine / CH₂Cl₂ / 7 h / 0 °C

10.1: 87 percent / Dess-Martin periodinane; 2,6-lutidine / CH₂Cl₂ / 2 h

11.1: 96 percent / K₂CO₃ / methanol / 20 °C

12.1: 77 percent / PdCl₂(CH₃CN)2 / acetone; H₂O / 40 h / Heating

13.1: Zp₂ZrCl₂ / CH₂Cl₂ / 13 h / 20 °C

13.2: 82 percent / I₂ / CH₂Cl₂ / -30 - 30 °C

14.1: 90 percent / Dess-Martin periodinane; 2,6-lutidine / CH₂Cl₂ / 1 h

15.1: 21 percent / NiCl₂; CrCl₂ / tetrahydrofuran; dimethylsulfoxide / 42 h

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; dichloro bis(acetonitrile) palladium(II); Grubbs catalyst first generation; tetrakis(triphenylphosphine) palladium⁽⁰⁾; zirconocene dichloride; bromocatecholborane; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; nickel dichloride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; 6.2: Stille coupling / 10.1: Dess-Martin oxidation / 14.1: Dess-Martin oxidation / 15.1: Kishi-Nozaki-Hiyama carbonyl addition reaction;
DOI:10.1021/jo0604585

Reference yield:

: 896104-74-8
(2S,3S,4E)-N-methoxy-2-{3-[(4-methoxybenzyl)oxy]propyl}-N,3-dimethylhex-4-enamide

: 896104-64-6
(1S,2S,3R)-2-{(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-3-[(4S,5S)-4-methyl-5-(3-methyl-but-3-enyl)-cyclopent-1-enyl]-but-2-enyl}-3-isopropyl-1-methyl-cyclopentanecarbaldehyde

Guidance literature:: Multi-step reaction with 14 steps

1.1: 82 percent / tetrahydrofuran / 20 °C

2.1: Grubbs catalyst / CH₂Cl₂ / Heating

3.1: H₂ / Pd/C / ethyl acetate / 2 h

4.1: LHMDS / toluene / 1 h / -78 °C

4.2: tetrahydrofuran / 4 h / -78 - 20 °C

5.1: HSnBu₃; Pd(PPh₃)4 / tetrahydrofuran / 2 h

5.2: 1.18 percent / Pd(PPh₃)4; LiCl; CuCl / dimethylsulfoxide / 37 h / 60 °C

6.1: 87 percent / DIBAL-H / CH₂Cl₂ / -78 - 20 °C

7.1: 93 percent / imidazole / dimethylformamide / 18 h / 20 °C

8.1: 91 percent / catecholborane bromide; 2,6-lutidine / CH₂Cl₂ / 7 h / 0 °C

9.1: 87 percent / Dess-Martin periodinane; 2,6-lutidine / CH₂Cl₂ / 2 h

10.1: 96 percent / K₂CO₃ / methanol / 20 °C

11.1: 77 percent / PdCl₂(CH₃CN)2 / acetone; H₂O / 40 h / Heating

12.1: Zp₂ZrCl₂ / CH₂Cl₂ / 13 h / 20 °C

12.2: 82 percent / I₂ / CH₂Cl₂ / -30 - 30 °C

13.1: 90 percent / Dess-Martin periodinane; 2,6-lutidine / CH₂Cl₂ / 1 h

14.1: 21 percent / NiCl₂; CrCl₂ / tetrahydrofuran; dimethylsulfoxide / 42 h

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; dichloro bis(acetonitrile) palladium(II); Grubbs catalyst first generation; tetrakis(triphenylphosphine) palladium⁽⁰⁾; zirconocene dichloride; bromocatecholborane; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; nickel dichloride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; 5.2: Stille coupling / 9.1: Dess-Martin oxidation / 13.1: Dess-Martin oxidation / 14.1: Kishi-Nozaki-Hiyama carbonyl addition reaction;
DOI:10.1021/jo0604585