(4E,7Z)-(2S,6S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-[(4S,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,6-dimethyl-nona-4,7-dien-3-one

Base Information

Chemical Name:(4E,7Z)-(2S,6S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-[(4S,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,6-dimethyl-nona-4,7-dien-3-one
CAS No.:851676-70-5
Molecular Formula:C₂₉H₄₆O₅Si
Molecular Weight:502.767
Hs Code.:

Synonyms:(4E,7Z)-(2S,6S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-[(4S,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,6-dimethyl-nona-4,7-dien-3-one

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Chemical Property of (4E,7Z)-(2S,6S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-[(4S,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,6-dimethyl-nona-4,7-dien-3-one

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Technology Process of (4E,7Z)-(2S,6S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-[(4S,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,6-dimethyl-nona-4,7-dien-3-one

There total 11 articles about (4E,7Z)-(2S,6S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-[(4S,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,6-dimethyl-nona-4,7-dien-3-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: 63.0%

: 851676-69-2
(6E,9Z)-(2R,3S,4S,8S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-1-(4-methoxy-benzyloxy)-2,6,8-trimethyl-undeca-6,9-dien-5-one

: 851676-70-5
(4E,7Z)-(2S,6S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-[(4S,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,6-dimethyl-nona-4,7-dien-3-one

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0 ℃;
DOI:10.1055/s-2005-862391

Reference yield:

: 851676-67-0
(4E,7Z)-(S)-3-Hydroxy-4,6-dimethyl-nona-4,7-dienoic acid ethyl ester

: 851676-70-5
(4E,7Z)-(2S,6S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-[(4S,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,6-dimethyl-nona-4,7-dien-3-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 93 percent / DIBALH / tetrahydrofuran / -78 °C

2.1: 90 percent / imidazole / CH₂Cl₂

3.1: Dess-Martin reagent / CH₂Cl₂ / 0 °C

4.1: Cy₂BCl; Et₃N / 16 h / -5 °C

4.2: 16 h / -78 - -25 °C

5.1: 63 percent / DDQ; MS / CH₂Cl₂ / 0 °C

With 1H-imidazole; dicyclohexylboron chloride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; 3.1: Dess-Martin oxidation;
DOI:10.1055/s-2005-862391

Reference yield:

: C₂₅H₂₆O

: 851676-70-5
(4E,7Z)-(2S,6S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-[(4S,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,6-dimethyl-nona-4,7-dien-3-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: 78 percent / p-TsOH / methanol; CH₂Cl₂

2.1: Dess-Martin reagent / CH₂Cl₂ / 0 °C

3.1: DIBALH / tetrahydrofuran / -78 °C

4.1: 90 percent / MnO₂ / diethyl ether

5.1: 86 percent / LDA / tetrahydrofuran / -78 °C

6.1: 93 percent / DIBALH / tetrahydrofuran / -78 °C

7.1: 90 percent / imidazole / CH₂Cl₂

8.1: Dess-Martin reagent / CH₂Cl₂ / 0 °C

9.1: Cy₂BCl; Et₃N / 16 h / -5 °C

9.2: 16 h / -78 - -25 °C

10.1: 63 percent / DDQ; MS / CH₂Cl₂ / 0 °C

With 1H-imidazole; manganese(IV) oxide; dicyclohexylboron chloride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2.1: Dess-Martin oxidation / 9.1: Dess-Martin oxidation;
DOI:10.1055/s-2005-862391