(2E,8Z)-(4R,5S,7S,10S,11R,12S,14R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,10,12,14-tetramethyl-pentadeca-2,8-diene-1,11-diol

Base Information

Chemical Name:(2E,8Z)-(4R,5S,7S,10S,11R,12S,14R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,10,12,14-tetramethyl-pentadeca-2,8-diene-1,11-diol
CAS No.:887602-39-3
Molecular Formula:C₃₉H₇₂O₆Si₂
Molecular Weight:693.168
Hs Code.:

(2E,8Z)-(4R,5S,7S,10S,11R,12S,14R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,10,12,14-tetramethyl-pentadeca-2,8-diene-1,11-diol

Synonyms:(2E,8Z)-(4R,5S,7S,10S,11R,12S,14R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,10,12,14-tetramethyl-pentadeca-2,8-diene-1,11-diol

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Chemical Property of (2E,8Z)-(4R,5S,7S,10S,11R,12S,14R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,10,12,14-tetramethyl-pentadeca-2,8-diene-1,11-diol

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Technology Process of (2E,8Z)-(4R,5S,7S,10S,11R,12S,14R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,10,12,14-tetramethyl-pentadeca-2,8-diene-1,11-diol

There total 12 articles about (2E,8Z)-(4R,5S,7S,10S,11R,12S,14R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,10,12,14-tetramethyl-pentadeca-2,8-diene-1,11-diol 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:

: 887602-29-1
5,7-bis-(tert-butyl-dimethyl-silanyloxy)-11-hydroxy-15-(4-methoxy-benzyloxy)-4,10,12,14-tetramethyl-pentadeca-2,8-dienoic acid ethyl ester

: 887602-39-3
(2E,8Z)-(4R,5S,7S,10S,11R,12S,14R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,10,12,14-tetramethyl-pentadeca-2,8-diene-1,11-diol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 - 0 ℃; for 0.5h;
DOI:10.1021/ja0609708

Reference yield:

: (2S,3S,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-hept-6-enal

: 887602-39-3
(2E,8Z)-(4R,5S,7S,10S,11R,12S,14R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,10,12,14-tetramethyl-pentadeca-2,8-diene-1,11-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 0.250 g / 2-methyl-2-butene; KH₂PO₄; NaClO₂ / tetrahydrofuran; H₂O / 2.5 h / 20 °C

2: 90 percent / Et₃N; DMAP; 2,4,6-trichlorobenzoyl chloride / toluene / -78 - 20 °C

3: DIBAL-H / toluene; CH₂Cl₂ / 0.25 h / -100 °C

4: 148 mg / CH₂Cl₂ / 0 - 20 °C

5: DIBAL-H / CH₂Cl₂ / 0.5 h / -78 - 0 °C

With dmap; sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1021/ja0609708

Reference yield:

: (E)-(5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-6-methyl-hept-2-enal

: 887602-39-3
(2E,8Z)-(4R,5S,7S,10S,11R,12S,14R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,10,12,14-tetramethyl-pentadeca-2,8-diene-1,11-diol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 460 mg / DIBAL-H / CH₂Cl₂ / -78 - 0 °C

2.1: (+)-diethyltartrate; Ti(i-PrO)4; tert-butyl hydrogen peroxide / CH₂Cl₂; toluene / 15 h / -20 °C

3.1: PPh₃; imidazole; I₂ / tetrahydrofuran; acetonitrile / 0.75 h / 0 °C

3.2: Zn / tetrahydrofuran; acetonitrile / 0.5 h / Heating

4.1: 464 mg / imidazole / CH₂Cl₂ / 0 - 20 °C

5.1: DDQ / CH₂Cl₂ / 0.25 h / 0 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

7.1: 0.250 g / 2-methyl-2-butene; KH₂PO₄; NaClO₂ / tetrahydrofuran; H₂O / 2.5 h / 20 °C

8.1: 90 percent / Et₃N; DMAP; 2,4,6-trichlorobenzoyl chloride / toluene / -78 - 20 °C

9.1: DIBAL-H / toluene; CH₂Cl₂ / 0.25 h / -100 °C

10.1: 148 mg / CH₂Cl₂ / 0 - 20 °C

11.1: DIBAL-H / CH₂Cl₂ / 0.5 h / -78 - 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; iodine; diisobutylaluminium hydride; Dess-Martin periodane; (+)-Weinsaeure-diethylester; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/ja0609708