(4E,6Z)-6-Bromo-7-{(4S,5R)-5-[(3E,5E)-(1S,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-1,5,7-trimethyl-2-oxo-8-triethylsilanyloxy-deca-3,5-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-4,6-dienoic acid

Base Information

Chemical Name:(4E,6Z)-6-Bromo-7-{(4S,5R)-5-[(3E,5E)-(1S,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-1,5,7-trimethyl-2-oxo-8-triethylsilanyloxy-deca-3,5-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-4,6-dienoic acid
CAS No.:179943-96-5
Molecular Formula:C₄₇H₆₉BrO₇Si₂
Molecular Weight:882.136
Hs Code.:

(4E,6Z)-6-Bromo-7-{(4S,5R)-5-[(3E,5E)-(1S,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-1,5,7-trimethyl-2-oxo-8-triethylsilanyloxy-deca-3,5-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-4,6-dienoic acid

Synonyms:(4E,6Z)-6-Bromo-7-{(4S,5R)-5-[(3E,5E)-(1S,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-1,5,7-trimethyl-2-oxo-8-triethylsilanyloxy-deca-3,5-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-4,6-dienoic acid

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Chemical Property of (4E,6Z)-6-Bromo-7-{(4S,5R)-5-[(3E,5E)-(1S,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-1,5,7-trimethyl-2-oxo-8-triethylsilanyloxy-deca-3,5-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-4,6-dienoic acid

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Technology Process of (4E,6Z)-6-Bromo-7-{(4S,5R)-5-[(3E,5E)-(1S,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-1,5,7-trimethyl-2-oxo-8-triethylsilanyloxy-deca-3,5-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-4,6-dienoic acid

There total 13 articles about (4E,6Z)-6-Bromo-7-{(4S,5R)-5-[(3E,5E)-(1S,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-1,5,7-trimethyl-2-oxo-8-triethylsilanyloxy-deca-3,5-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-4,6-dienoic acid 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: 70.0%

: 179943-82-9
(4E,6Z)-6-Bromo-7-{(4S,5R)-5-[(3E,5E)-(1S,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-1,5,7-trimethyl-2-oxo-8-triethylsilanyloxy-deca-3,5-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-4,6-dienoic acid benzyl ester

: 179943-96-5
(4E,6Z)-6-Bromo-7-{(4S,5R)-5-[(3E,5E)-(1S,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-1,5,7-trimethyl-2-oxo-8-triethylsilanyloxy-deca-3,5-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-4,6-dienoic acid

Guidance literature:: With lithium hydroxide; In 1,2-dimethoxyethane; for 3h; Ambient temperature;
DOI:10.1021/ja9607796

Reference yield:

: 6089-09-4
4-pentynoic acid

: 179943-96-5
(4E,6Z)-6-Bromo-7-{(4S,5R)-5-[(3E,5E)-(1S,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-1,5,7-trimethyl-2-oxo-8-triethylsilanyloxy-deca-3,5-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-4,6-dienoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / DBU / acetonitrile / Ambient temperature

2: 1.) catecholborane, 2.) aq. NaCl, 3.) aq. TlOH, Pd₂(dba)3, Ph₃P

3: 70 percent / aq. LiOH / 1,2-dimethoxy-ethane / 3 h / Ambient temperature

With lithium hydroxide; TlOH; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; sodium chloride; benzo[1,3,2]dioxaborole; In 1,2-dimethoxyethane; acetonitrile;
DOI:10.1021/ja9607796

Reference yield:

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 179943-96-5
(4E,6Z)-6-Bromo-7-{(4S,5R)-5-[(3E,5E)-(1S,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-1,5,7-trimethyl-2-oxo-8-triethylsilanyloxy-deca-3,5-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-4,6-dienoic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 99 percent / 2,4-lutidine / CH₂Cl₂ / 0.42 h / -78 - 0 °C

2: 84 percent / DIBAL-H / CH₂Cl₂; tetrahydrofuran / 3 h / -78 °C

3: 94 percent / MnO₂ / CH₂Cl₂ / 48 h / Ambient temperature

4: 1.) LiN(TMS)2 / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 15 min

5: 1.) Ac₂O, DMAP, 2.) DBU / 1.) THF, RT, 30 min, 2.) THF, RT, 30 min

6: 1.) catecholborane, 2.) aq. NaCl, 3.) aq. TlOH, Pd₂(dba)3, Ph₃P

7: 70 percent / aq. LiOH / 1,2-dimethoxy-ethane / 3 h / Ambient temperature

With dmap; manganese(IV) oxide; lithium hydroxide; TlOH; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; 2,4-lutidine; acetic anhydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; sodium chloride; lithium hexamethyldisilazane; benzo[1,3,2]dioxaborole; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/ja9607796