(3Z,9E)-(5S,6S,7R,11R,13S,14R,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6,16-bis-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-hexadeca-1,3,9-trien-8-one

Base Information

Chemical Name:(3Z,9E)-(5S,6S,7R,11R,13S,14R,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6,16-bis-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-hexadeca-1,3,9-trien-8-one
CAS No.:792911-24-1
Molecular Formula:C₄₃H₆₆O₆Si
Molecular Weight:707.079
Hs Code.:

(3Z,9E)-(5S,6S,7R,11R,13S,14R,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6,16-bis-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-hexadeca-1,3,9-trien-8-one

Synonyms:(3Z,9E)-(5S,6S,7R,11R,13S,14R,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6,16-bis-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-hexadeca-1,3,9-trien-8-one

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Chemical Property of (3Z,9E)-(5S,6S,7R,11R,13S,14R,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6,16-bis-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-hexadeca-1,3,9-trien-8-one

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Technology Process of (3Z,9E)-(5S,6S,7R,11R,13S,14R,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6,16-bis-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-hexadeca-1,3,9-trien-8-one

There total 14 articles about (3Z,9E)-(5S,6S,7R,11R,13S,14R,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6,16-bis-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-hexadeca-1,3,9-trien-8-one 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%

: 792911-19-4
(2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanal

: 792911-20-7
[4-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-nona-6,8-dienyl]-phosphonic-acid dimethyl ester

: 792911-24-1
(3Z,9E)-(5S,6S,7R,11R,13S,14R,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6,16-bis-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-hexadeca-1,3,9-trien-8-one

Guidance literature:: [4-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-nona-6,8-dienyl]-phosphonic-acid dimethyl ester; With barium hydroxide octahydrate; In tetrahydrofuran; for 1h;

(2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanal; In tetrahydrofuran; water; for 18h;

Reference yield:

: 792911-22-9
(-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol

: 792911-24-1
(3Z,9E)-(5S,6S,7R,11R,13S,14R,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6,16-bis-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-hexadeca-1,3,9-trien-8-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 86 percent / PPh₃; I₂; imidazole / toluene / 0.25 h / 0 °C

2.1: LiCl; lithium diisopropylamide / tetrahydrofuran / -78 - 20 °C

2.2: tetrahydrofuran / 18 h / 0 - 20 °C

3.1: LiNH₂BH₃ / tetrahydrofuran / 18 h / 0 - 20 °C

4.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 0 °C

5.1: Ba(OH)2*8H₂O / tetrahydrofuran / 1 h

5.2: 92 percent / tetrahydrofuran; H₂O / 20 h

With 1H-imidazole; barium dihydroxide; lithium amidotrihydroborate; iodine; sodium hydrogencarbonate; Dess-Martin periodane; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; 1.1: modified Mitsunobu reaction / 5.1: Horner-Wadsworth-Emmons coupling;
DOI:10.1002/anie.200460589

Reference yield:

: 860477-26-5
[(Z)-(3S,4S,5S)-2-Hydroxy-4-(4-methoxy-benzyloxy)-3,5-dimethyl-nona-6,8-dienyl]-phosphonic acid dimethyl ester

: 792911-24-1
(3Z,9E)-(5S,6S,7R,11R,13S,14R,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6,16-bis-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-hexadeca-1,3,9-trien-8-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / 20 °C

2.1: Ba(OH)2*8H₂O / tetrahydrofuran / 1 h

2.2: 92 percent / tetrahydrofuran; H₂O / 20 h

With barium dihydroxide; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 2.1: Horner-Wadsworth-Emmons coupling;
DOI:10.1002/anie.200460589