7,13-Pentadecadien-1-ol, 9,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)meth oxy]-2,4,6,12-tetramethyl-15-(triphenylmethoxy)-, (2S,4S,5R,6S,7Z,9S,11S,12S,13E)-

Base Information

Chemical Name:7,13-Pentadecadien-1-ol, 9,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)meth oxy]-2,4,6,12-tetramethyl-15-(triphenylmethoxy)-, (2S,4S,5R,6S,7Z,9S,11S,12S,13E)-
CAS No.:672296-44-5
Molecular Formula:C58H86O6Si2
Molecular Weight:935.488
Hs Code.:

7,13-Pentadecadien-1-ol,
9,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)meth
oxy]-2,4,6,12-tetramethyl-15-(triphenylmethoxy)-,
(2S,4S,5R,6S,7Z,9S,11S,12S,13E)-

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Chemical Property of 7,13-Pentadecadien-1-ol, 9,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)meth oxy]-2,4,6,12-tetramethyl-15-(triphenylmethoxy)-, (2S,4S,5R,6S,7Z,9S,11S,12S,13E)-

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Technology Process of 7,13-Pentadecadien-1-ol, 9,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)meth oxy]-2,4,6,12-tetramethyl-15-(triphenylmethoxy)-, (2S,4S,5R,6S,7Z,9S,11S,12S,13E)-

There total 18 articles about 7,13-Pentadecadien-1-ol, 9,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)meth oxy]-2,4,6,12-tetramethyl-15-(triphenylmethoxy)-, (2S,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: 87.0%

: 672296-43-4
4(S)-benzyl-3-[9(S),11(S)-bis(tert-butyldimethylsilanyloxy)-5(R)-(4-methoxybenzyloxy)-2(S),4(S),6(S),12(S)-tetramethyl-15-trityloxy-pentadeca-7,13-dienoyl]oxazolidin-2-one

: 672296-44-5
(2S,4S,5R,6S,9S,11S,12S)-9,11-bis(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2,4,6,12-tetramethyl-15-trityloxypentadeca-7,13-dien-1-ol

Guidance literature:: With lithium borohydride; In tetrahydrofuran; methanol; at 0 ℃; for 2h;
DOI:10.1016/j.tet.2007.05.033

Reference yield:

: 672296-32-1
(4R,5S,7S)-5,7,8-tris(tert-butyldimethylsilanyloxy)-4-methyloct-2-enoic acid ethyl ester

: 672296-44-5
(2S,4S,5R,6S,9S,11S,12S)-9,11-bis(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2,4,6,12-tetramethyl-15-trityloxypentadeca-7,13-dien-1-ol

Guidance literature:: Multi-step reaction with 14 steps

1.1: 65 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 20 °C

2.1: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

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

3.2: 75 percent / tetrahydrofuran / -78 - 20 °C

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

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

5.2: 1.79 g / NaBH₄ / tetrahydrofuran; H₂O / 0 °C

6.1: 99 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating

7.1: 74 percent / diisobutylaluminum hydride / hexane; CH₂Cl₂ / -78 - 0 °C

8.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

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

9.2: 2.01 g / tetrahydrofuran / 3 h / -78 - 0 °C

10.1: 97 percent / NiCl₂*6H₂O; NaBH₄ / methanol; tetrahydrofuran / 0 °C

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

12.1: Et₃N / tetrahydrofuran / -78 - 0 °C

12.2: 1.52 g / LiCl / tetrahydrofuran / 0 - 20 °C

13.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

13.2: 62 percent / tetrahydrofuran / 4 h / -78 °C

14.1: 87 percent / LiBH₄ / methanol; tetrahydrofuran / 2 h / 0 °C

With pyridine; dmap; potassium hydroxide; sodium tetrahydroborate; lithium borohydride; potassium tert-butylate; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; nickel dichloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; 2.1: Dess-Martin oxidation / 3.2: Wittig coupling / 8.1: Dess-Martin oxidation / 9.2: Horner-Wadsworth-Emmons reaction;
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

: 672296-44-5
(2S,4S,5R,6S,9S,11S,12S)-9,11-bis(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2,4,6,12-tetramethyl-15-trityloxypentadeca-7,13-dien-1-ol

Guidance literature:: Multi-step reaction with 13 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

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

11.1: Et₃N / tetrahydrofuran / -78 - 0 °C

11.2: 1.52 g / LiCl / tetrahydrofuran / 0 - 20 °C

12.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

12.2: 62 percent / tetrahydrofuran / 4 h / -78 °C

13.1: 87 percent / LiBH₄ / methanol; tetrahydrofuran / 2 h / 0 °C

With pyridine; dmap; potassium hydroxide; sodium tetrahydroborate; lithium borohydride; 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