7,13-Pentadecadienoic acid, 9,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)meth oxy]-4,6,12-trimethyl-15-(triphenylmethoxy)-, ethyl ester, (4S,5R,6S,7Z,9S,11S,12S,13E)-

Base Information

Chemical Name:7,13-Pentadecadienoic acid, 9,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)meth oxy]-4,6,12-trimethyl-15-(triphenylmethoxy)-, ethyl ester, (4S,5R,6S,7Z,9S,11S,12S,13E)-
CAS No.:672296-40-1
Molecular Formula:C59H86O7Si2
Molecular Weight:963.499
Hs Code.:

7,13-Pentadecadienoic acid,
9,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)meth
oxy]-4,6,12-trimethyl-15-(triphenylmethoxy)-, ethyl ester,
(4S,5R,6S,7Z,9S,11S,12S,13E)-

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Chemical Property of 7,13-Pentadecadienoic acid, 9,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)meth oxy]-4,6,12-trimethyl-15-(triphenylmethoxy)-, ethyl ester, (4S,5R,6S,7Z,9S,11S,12S,13E)-

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Technology Process of 7,13-Pentadecadienoic acid, 9,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)meth oxy]-4,6,12-trimethyl-15-(triphenylmethoxy)-, ethyl ester, (4S,5R,6S,7Z,9S,11S,12S,13E)-

There total 13 articles about 7,13-Pentadecadienoic acid, 9,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)meth oxy]-4,6,12-trimethyl-15-(triphenylmethoxy)-, ethyl ester, (4S,5R,6S,7Z,9S,11S,12S,13E)- 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: 97.0%

: 672296-39-8
(4S,5S,6S,9S,11S,12S)-9,11-bis(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-4,6,12-trimethyl-15-trityloxypentadeca-2,7,13-trienoic acid ethyl ester

: 672296-40-1
(4S,5R,6S,9S,11S,12S)-9,11-bis(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-4,6,12-trimethyl-15-trityloxypentadeca-7,13-dienoic acid ethyl ester

Guidance literature:: With sodium tetrahydroborate; nickel dichloride; In tetrahydrofuran; methanol; at 0 ℃;
DOI:10.1016/j.tet.2007.05.033

Reference yield:

: 672296-33-2
(4R,5S,7S)-5,7-bis(tert-butyldimethylsilanyloxy)-8-hydroxy-4-methyloct-2-enoic acid ethyl ester

: 672296-40-1
(4S,5R,6S,9S,11S,12S)-9,11-bis(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-4,6,12-trimethyl-15-trityloxypentadeca-7,13-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

2.1: NaHMDS / tetrahydrofuran / -78 - 20 °C

2.2: 75 percent / tetrahydrofuran / -78 - 20 °C

3.1: aq. KOH / ethanol; tetrahydrofuran / 6 h / Heating

4.1: Et₃N / tetrahydrofuran / 0.25 h / -10 °C

4.2: 1.79 g / NaBH₄ / tetrahydrofuran; H₂O / 0 °C

5.1: 99 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating

6.1: 74 percent / diisobutylaluminum hydride / hexane; CH₂Cl₂ / -78 - 0 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

8.1: potassium tert-butoxide / tetrahydrofuran / 0.5 h / -78 °C

8.2: 2.01 g / tetrahydrofuran / 3 h / -78 - 0 °C

9.1: 97 percent / NiCl₂*6H₂O; NaBH₄ / methanol; tetrahydrofuran / 0 °C

With pyridine; dmap; potassium hydroxide; sodium tetrahydroborate; potassium tert-butylate; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; nickel dichloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; 1.1: Dess-Martin oxidation / 2.2: Wittig coupling / 7.1: Dess-Martin oxidation / 8.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.05.033

Reference yield:

: C₁₁H₂₀O₅

: 672296-40-1
(4S,5R,6S,9S,11S,12S)-9,11-bis(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-4,6,12-trimethyl-15-trityloxypentadeca-7,13-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 2.96 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

2.1: 65 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 20 °C

3.1: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

4.1: NaHMDS / tetrahydrofuran / -78 - 20 °C

4.2: 75 percent / tetrahydrofuran / -78 - 20 °C

5.1: aq. KOH / ethanol; tetrahydrofuran / 6 h / Heating

6.1: Et₃N / tetrahydrofuran / 0.25 h / -10 °C

6.2: 1.79 g / NaBH₄ / tetrahydrofuran; H₂O / 0 °C

7.1: 99 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating

8.1: 74 percent / diisobutylaluminum hydride / hexane; CH₂Cl₂ / -78 - 0 °C

9.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

10.1: potassium tert-butoxide / tetrahydrofuran / 0.5 h / -78 °C

10.2: 2.01 g / tetrahydrofuran / 3 h / -78 - 0 °C

11.1: 97 percent / NiCl₂*6H₂O; NaBH₄ / methanol; tetrahydrofuran / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium tetrahydroborate; potassium tert-butylate; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; nickel dichloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; 3.1: Dess-Martin oxidation / 4.2: Wittig coupling / 9.1: Dess-Martin oxidation / 10.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.05.033