(1R,4R)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methyl-2-cyclohexen-1-ol

Base Information

Chemical Name:(1R,4R)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methyl-2-cyclohexen-1-ol
CAS No.:762263-85-4
Molecular Formula:C₄₀H₇₄O₃Si₂
Molecular Weight:659.197
Hs Code.:

(1R,4R)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methyl-2-cyclohexen-1-ol

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Chemical Property of (1R,4R)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methyl-2-cyclohexen-1-ol

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Technology Process of (1R,4R)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methyl-2-cyclohexen-1-ol

There total 22 articles about (1R,4R)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methyl-2-cyclohexen-1-ol 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:

: (S)-2-Methoxy-2-naphthalen-1-yl-propionic acid (1R,4R)-4-[(2E,6Z)-7-(tert-butyl-dimethyl-silanyloxymethyl)-3,11-dimethyl-dodeca-2,6,10-trienyl]-2-[(E)-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-pent-3-enyl]-3-methyl-cyclohex-2-enyl ester

: 762263-85-4
(1R,4R)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methyl-2-cyclohexen-1-ol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at -78 - 0 ℃; for 3h;
DOI:10.1039/b406820c

Reference yield:

: 106-24-1
Geraniol

: 762263-85-4
(1R,4R)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methyl-2-cyclohexen-1-ol

Guidance literature:: Multi-step reaction with 14 steps

1.1: 98 percent / imidazole / dimethylformamide

2.1: 81 percent / m-CPBA / CHCl₃ / 1 h / 0 °C

3.1: aq. HIO₄ / tetrahydrofuran / 0.5 h / 0 °C

4.1: 17.1 g / imidazole / dimethylformamide / 0.5 h / 20 °C

5.1: 92 percent / aq. AcOH / tetrahydrofuran / 19 h / 20 °C

6.1: PBr₃; pyridine / diethyl ether / 1 h / -40 - -20 °C

7.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: 93 percent / tetrahydrofuran; hexane / 1 h / 20 °C

8.1: 91 percent / tetrahydrofuran / 3 h / 20 °C

9.1: 84.6 percent / L-Selectride / tetrahydrofuran / 4 h / -60 °C

10.1: 83 percent / DMAP; DCC / CH₂Cl₂ / 46 h / 20 °C

11.1: 749 mg / TBAF / tetrahydrofuran / 3 h / 20 °C

12.1: imidazole / dimethylformamide / 0.5 h / 20 °C

13.1: 568 mg / LiAlH₄ / diethyl ether / 3 h / -78 - 0 °C

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; phosphorus tribromide; L-Selectride; acetic acid; periodic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1039/b406820c

Reference yield:

: 37567-78-5
1,5-dimethoxy-1,4-cyclohexadiene

: 762263-85-4
(1R,4R)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methyl-2-cyclohexen-1-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: t-BuLi / pentane; tetrahydrofuran / 1 h / -78 °C

1.2: 69 percent / pentane; tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C

2.1: aq. HCl / tetrahydrofuran / 1 h / 20 °C

3.1: methanol; ethyl acetate; diethyl ether / 0.5 h / 0 °C

4.1: 2.66 g / imidazole / dimethylformamide / 1 h / 20 °C

5.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: 93 percent / tetrahydrofuran; hexane / 1 h / 20 °C

6.1: 91 percent / tetrahydrofuran / 3 h / 20 °C

7.1: 84.6 percent / L-Selectride / tetrahydrofuran / 4 h / -60 °C

8.1: 83 percent / DMAP; DCC / CH₂Cl₂ / 46 h / 20 °C

9.1: 749 mg / TBAF / tetrahydrofuran / 3 h / 20 °C

10.1: imidazole / dimethylformamide / 0.5 h / 20 °C

11.1: 568 mg / LiAlH₄ / diethyl ether / 3 h / -78 - 0 °C

With 1H-imidazole; hydrogenchloride; dmap; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; tert.-butyl lithium; L-Selectride; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; pentane;
DOI:10.1039/b406820c