(2Z,4S,5E,7S,8S,9S,10R)-8-(tert-butyldimethylsilyloxymethyl)-9,11-[(S)-3,4-dimethoxybenzylidenedioxy]-7-methoxymethyl-4,6,10-trimethyl-2,5-undecadiene

Base Information

Chemical Name:(2Z,4S,5E,7S,8S,9S,10R)-8-(tert-butyldimethylsilyloxymethyl)-9,11-[(S)-3,4-dimethoxybenzylidenedioxy]-7-methoxymethyl-4,6,10-trimethyl-2,5-undecadiene
CAS No.:240821-29-8
Molecular Formula:C₃₂H₅₄O₇Si
Molecular Weight:578.862
Hs Code.:

(2Z,4S,5E,7S,8S,9S,10R)-8-(tert-butyldimethylsilyloxymethyl)-9,11-[(S)-3,4-dimethoxybenzylidenedioxy]-7-methoxymethyl-4,6,10-trimethyl-2,5-undecadiene

Synonyms:(2Z,4S,5E,7S,8S,9S,10R)-8-(tert-butyldimethylsilyloxymethyl)-9,11-[(S)-3,4-dimethoxybenzylidenedioxy]-7-methoxymethyl-4,6,10-trimethyl-2,5-undecadiene

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Chemical Property of (2Z,4S,5E,7S,8S,9S,10R)-8-(tert-butyldimethylsilyloxymethyl)-9,11-[(S)-3,4-dimethoxybenzylidenedioxy]-7-methoxymethyl-4,6,10-trimethyl-2,5-undecadiene

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Technology Process of (2Z,4S,5E,7S,8S,9S,10R)-8-(tert-butyldimethylsilyloxymethyl)-9,11-[(S)-3,4-dimethoxybenzylidenedioxy]-7-methoxymethyl-4,6,10-trimethyl-2,5-undecadiene

There total 31 articles about (2Z,4S,5E,7S,8S,9S,10R)-8-(tert-butyldimethylsilyloxymethyl)-9,11-[(S)-3,4-dimethoxybenzylidenedioxy]-7-methoxymethyl-4,6,10-trimethyl-2,5-undecadiene 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: 100.0%

: 107-30-2
chloromethyl methyl ether

: 240821-26-5
(2Z,4S,5E,7S,8S,9S,10R)-8-(tert-butyldimethylsilyloxymethyl)-9,11-[(S)-3,4-dimethoxybenzylidenedioxy]-4,6,10-trimethyl-2,5-undecadien-7-ol

: 240821-29-8
(2Z,4S,5E,7S,8S,9S,10R)-8-(tert-butyldimethylsilyloxymethyl)-9,11-[(S)-3,4-dimethoxybenzylidenedioxy]-7-methoxymethyl-4,6,10-trimethyl-2,5-undecadiene

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; Ambient temperature;
DOI:10.1055/s-1999-2730

Reference yield:

: (2R,3E,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-ol

: 240821-29-8
(2Z,4S,5E,7S,8S,9S,10R)-8-(tert-butyldimethylsilyloxymethyl)-9,11-[(S)-3,4-dimethoxybenzylidenedioxy]-7-methoxymethyl-4,6,10-trimethyl-2,5-undecadiene

Guidance literature:: Multi-step reaction with 11 steps

1.1: 91 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

2.1: 99 percent / PPTS / ethanol / 6 h / 50 - 55 °C

3.1: 96 percent / Zn(BH₄)2 / diethyl ether / 7 h / 0 °C

4.1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 10.5 h / 0 °C

5.1: 100 percent / TBAF; AcOH / tetrahydrofuran / 144 h / 20 °C

6.1: 93 percent / DDQ / CH₂Cl₂ / 0.58 h / -10 °C

7.1: 100 percent / Dess-Martin periodinane; Py / CH₂Cl₂ / 0.5 h / 20 °C

8.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C

8.2: tetrahydrofuran / 38 h / 20 °C

9.1: 74 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

10.1: 86 percent / imidazole / CH₂Cl₂ / 72 h / 20 °C

11.1: 100 percent / iso-Pr₂EtN / CH₂Cl₂ / 168 h / 20 °C

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 1.1: Oxidation / 2.1: Hydrolysis / 3.1: Hydrogenolysis / 4.1: Acetylation / 5.1: desilylation / 6.1: Cyclization / 7.1: Oxidation / 8.1: Metallation / 8.2: olefination / 9.1: Hydrogenolysis / 10.1: Substitution / 11.1: Substitution;
DOI:10.1248/cpb.47.1288

Reference yield:

: 240821-06-1
(2R,3E,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-one

: 240821-29-8
(2Z,4S,5E,7S,8S,9S,10R)-8-(tert-butyldimethylsilyloxymethyl)-9,11-[(S)-3,4-dimethoxybenzylidenedioxy]-7-methoxymethyl-4,6,10-trimethyl-2,5-undecadiene

Guidance literature:: Multi-step reaction with 10 steps

1.1: 99 percent / PPTS / ethanol / 6 h / 50 - 55 °C

2.1: 96 percent / Zn(BH₄)2 / diethyl ether / 7 h / 0 °C

3.1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 10.5 h / 0 °C

4.1: 100 percent / TBAF; AcOH / tetrahydrofuran / 144 h / 20 °C

5.1: 93 percent / DDQ / CH₂Cl₂ / 0.58 h / -10 °C

6.1: 100 percent / Dess-Martin periodinane; Py / CH₂Cl₂ / 0.5 h / 20 °C

7.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C

7.2: tetrahydrofuran / 38 h / 20 °C

8.1: 74 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

9.1: 86 percent / imidazole / CH₂Cl₂ / 72 h / 20 °C

10.1: 100 percent / iso-Pr₂EtN / CH₂Cl₂ / 168 h / 20 °C

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 1.1: Hydrolysis / 2.1: Hydrogenolysis / 3.1: Acetylation / 4.1: desilylation / 5.1: Cyclization / 6.1: Oxidation / 7.1: Metallation / 7.2: olefination / 8.1: Hydrogenolysis / 9.1: Substitution / 10.1: Substitution;
DOI:10.1248/cpb.47.1288