13,15-Hexadecadienal, 3,9-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)meth oxy]-2,4,6,10,12-pentamethyl-, (2R,3R,4S,6S,9R,10R,11S,12S,13Z)-

Base Information

Chemical Name:13,15-Hexadecadienal, 3,9-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)meth oxy]-2,4,6,10,12-pentamethyl-, (2R,3R,4S,6S,9R,10R,11S,12S,13Z)-
CAS No.:919298-97-8
Molecular Formula:C41H74O5Si2
Molecular Weight:703.207
Hs Code.:

13,15-Hexadecadienal,
3,9-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)meth
oxy]-2,4,6,10,12-pentamethyl-, (2R,3R,4S,6S,9R,10R,11S,12S,13Z)-

Synonyms:

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Chemical Property of 13,15-Hexadecadienal, 3,9-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)meth oxy]-2,4,6,10,12-pentamethyl-, (2R,3R,4S,6S,9R,10R,11S,12S,13Z)-

Chemical Property:

Purity/Quality:

Safty Information:

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Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of 13,15-Hexadecadienal, 3,9-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)meth oxy]-2,4,6,10,12-pentamethyl-, (2R,3R,4S,6S,9R,10R,11S,12S,13Z)-

There total 30 articles about 13,15-Hexadecadienal, 3,9-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)meth oxy]-2,4,6,10,12-pentamethyl-, (2R,3R,4S,6S,9R,10R,11S,12S,13Z)- 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: 94.0%

: 919298-96-7
(+)-(Z)-(2S,3R,4S,6S,9R,10R,11S,12S)-3,9-bis-(tert-butyldimethylsilanyloxy)-11-(4-methoxybenzyloxy)-2,4,6,10,12-pentamethylhexadeca-13,15-dien-1-ol

: 919298-97-8
(-)-(Z)-(2R,3R,4S,6S,9R,10R,11S,12S)-3,9-bis-(tert-butyldimethylsilanyloxy)-11-(4-methoxybenzyloxy)-2,4,6,10,12-pentamethylhexadeca-13,15-dienal

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ol062737k

Reference yield:

: 5,6-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-hexanal

: 919298-97-8
(-)-(Z)-(2R,3R,4S,6S,9R,10R,11S,12S)-3,9-bis-(tert-butyldimethylsilanyloxy)-11-(4-methoxybenzyloxy)-2,4,6,10,12-pentamethylhexadeca-13,15-dienal

Guidance literature:: Multi-step reaction with 14 steps

1.1: NaBH₄

2.1: 95 percent / MgSO₄; PPTS / toluene / 72 h / 80 °C

3.1: 90 percent / DIBAL-H / CH₂Cl₂ / -78 - 0 °C

4.1: 98 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 0 - 20 °C

5.1: 64 percent / p-TSA / methanol / 7 h / 0 - 20 °C

6.1: 96 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

7.1: 80 percent / NaHMDS / dimethylformamide; toluene / -60 - 20 °C

8.1: 98 percent / H₂ / Pd/C / cyclohexane / 24 h / 25857.4 Torr

9.1: 99 percent / MgSO₄; PPTS / toluene / 72 h / 80 °C

10.1: DIBAL-H / CH₂Cl₂ / -78 - -45 °C

11.1: 97 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.5 h / 0 °C

12.1: CrCl₃ / tetrahydrofuran / 0 - 20 °C

12.2: 95 percent / KH / tetrahydrofuran / 2.5 h / 0 °C

13.1: 84 percent / p-TSA / methanol / 1.5 h / 0 °C

14.1: 94 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

With chromium chloride; sodium tetrahydroborate; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; magnesium sulfate; Dess-Martin periodane; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; 6.1: Dess-Martin oxidation / 11.1: Dess-Martin oxidation / 14.1: Dess-Martin oxidation;
DOI:10.1021/ol062737k

Reference yield:

: 919298-77-4
1,3-bis(tert-butyldimethylsilyloxy)-5-iodo-2,4-dimethyl-pentane

: 919298-97-8
(-)-(Z)-(2R,3R,4S,6S,9R,10R,11S,12S)-3,9-bis-(tert-butyldimethylsilanyloxy)-11-(4-methoxybenzyloxy)-2,4,6,10,12-pentamethylhexadeca-13,15-dienal

Guidance literature:: Multi-step reaction with 12 steps

1.1: 93 percent / LiCl; n-BuLi; diisopropylamine / tetrahydrofuran / 32 h / 0 - 20 °C

2.1: 91 percent / n-BuLi; diisopropylamine; BH₃*NH₃ / tetrahydrofuran; hexane / 0 - 20 °C

3.1: 100 percent / PPh₃; DEAD / tetrahydrofuran / 0 - 20 °C

4.1: 93 percent / NaHCO₃; m-CPBA / CH₂Cl₂ / 16 h / 20 °C

5.1: 80 percent / NaHMDS / dimethylformamide; toluene / -60 - 20 °C

6.1: 98 percent / H₂ / Pd/C / cyclohexane / 24 h / 25857.4 Torr

7.1: 99 percent / MgSO₄; PPTS / toluene / 72 h / 80 °C

8.1: DIBAL-H / CH₂Cl₂ / -78 - -45 °C

9.1: 97 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.5 h / 0 °C

10.1: CrCl₃ / tetrahydrofuran / 0 - 20 °C

10.2: 95 percent / KH / tetrahydrofuran / 2.5 h / 0 °C

11.1: 84 percent / p-TSA / methanol / 1.5 h / 0 °C

12.1: 94 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

With chromium chloride; n-butyllithium; borane-ammonia complex; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; magnesium sulfate; Dess-Martin periodane; toluene-4-sulfonic acid; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium chloride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; 3.1: Mitsunobu reaction / 9.1: Dess-Martin oxidation / 12.1: Dess-Martin oxidation;
DOI:10.1021/ol062737k