2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-6-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methoxy-2-cyclohexen-1-one

Base Information

Chemical Name:2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-6-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methoxy-2-cyclohexen-1-one
CAS No.:762263-74-1
Molecular Formula:C₅₀H₇₆O₄Si₂
Molecular Weight:797.322
Hs Code.:

2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-6-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methoxy-2-cyclohexen-1-one

Synonyms:2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-6-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methoxy-2-cyclohexen-1-one

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Chemical Property of 2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-6-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methoxy-2-cyclohexen-1-one

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Technology Process of 2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-6-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methoxy-2-cyclohexen-1-one

There total 15 articles about 2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-6-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methoxy-2-cyclohexen-1-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: 93.0%

: 762263-73-0
2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-3-methoxy-2-cyclohexen-1-one

: 473312-91-3
(6Z,10E)-12-bromo-6-tert-butyldiphenylsilyloxymethyl-2,10-dimethyl-2,6,10-dodecatriene

: 762263-74-1
2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-6-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methoxy-2-cyclohexen-1-one

Guidance literature:: 2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-3-methoxy-2-cyclohexen-1-one; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

(6Z,10E)-12-bromo-6-tert-butyldiphenylsilyloxymethyl-2,10-dimethyl-2,6,10-dodecatriene; In tetrahydrofuran; hexane; at 20 ℃; for 1h;
DOI:10.1039/b406820c

Reference yield:

: 106-24-1
Geraniol

: 762263-74-1
2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-6-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methoxy-2-cyclohexen-1-one

Guidance literature:: Multi-step reaction with 8 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

With pyridine; 1H-imidazole; phosphorus tribromide; acetic acid; periodic acid; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; chloroform; N,N-dimethyl-formamide;
DOI:10.1039/b406820c

Reference yield:

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

: 762263-74-1
2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-6-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methoxy-2-cyclohexen-1-one

Guidance literature:: Multi-step reaction with 5 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

With 1H-imidazole; hydrogenchloride; tert.-butyl lithium; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; ethyl acetate; N,N-dimethyl-formamide; pentane;
DOI:10.1039/b406820c