(2S,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-3-(3,4-dimethoxybenzyloxy)-5-methoxymethoxy-2,6,8-trimethyl-6,9-undecadienal

Base Information

Chemical Name:(2S,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-3-(3,4-dimethoxybenzyloxy)-5-methoxymethoxy-2,6,8-trimethyl-6,9-undecadienal
CAS No.:252006-20-5
Molecular Formula:C₃₂H₅₄O₇Si
Molecular Weight:578.862
Hs Code.:

Synonyms:(2S,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-3-(3,4-dimethoxybenzyloxy)-5-methoxymethoxy-2,6,8-trimethyl-6,9-undecadienal

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Chemical Property of (2S,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-3-(3,4-dimethoxybenzyloxy)-5-methoxymethoxy-2,6,8-trimethyl-6,9-undecadienal

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Technology Process of (2S,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-3-(3,4-dimethoxybenzyloxy)-5-methoxymethoxy-2,6,8-trimethyl-6,9-undecadienal

There total 32 articles about (2S,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-3-(3,4-dimethoxybenzyloxy)-5-methoxymethoxy-2,6,8-trimethyl-6,9-undecadienal 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%

: 240821-31-2
(2R,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-3-(3,4-dimethoxybenzyloxy)-5-methoxymethoxy-2,6,8-trimethyl-6,9-undecadien-1-ol

: 252006-20-5
(2S,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-3-(3,4-dimethoxybenzyloxy)-5-methoxymethoxy-2,6,8-trimethyl-6,9-undecadienal

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 19h;
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

: 252006-20-5
(2S,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-3-(3,4-dimethoxybenzyloxy)-5-methoxymethoxy-2,6,8-trimethyl-6,9-undecadienal

Guidance literature:: Multi-step reaction with 12 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

11.1: 70 percent / DIBAH / hexane; CH₂Cl₂ / 13.5 h / -50 °C

12.1: 100 percent / Dess-Martin periodinane; Py / CH₂Cl₂ / 19 h / 20 °C

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; ethanol; hexane; 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 / 11.1: reductive cleavage / 12.1: Oxidation;
DOI:10.1248/cpb.47.1288

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

: 252006-20-5
(2S,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-3-(3,4-dimethoxybenzyloxy)-5-methoxymethoxy-2,6,8-trimethyl-6,9-undecadienal

Guidance literature:: Multi-step reaction with 13 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

12.1: 70 percent / DIBAH / hexane; CH₂Cl₂ / 13.5 h / -50 °C

13.1: 100 percent / Dess-Martin periodinane; Py / CH₂Cl₂ / 19 h / 20 °C

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; ethanol; hexane; 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 / 12.1: reductive cleavage / 13.1: Oxidation;
DOI:10.1248/cpb.47.1288