(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

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 benzyl ester
CAS No.:179943-82-9
Molecular Formula:C₅₄H₇₅BrO₇Si₂
Molecular Weight:972.26
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 benzyl ester

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 benzyl ester

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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 benzyl ester

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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 benzyl ester

There total 12 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 benzyl ester 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:

: 6089-09-4
4-pentynoic acid

: 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

Guidance literature:: Multi-step reaction with 2 steps

1: 82 percent / DBU / acetonitrile / Ambient temperature

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

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

Reference yield:

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 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

Guidance literature:: Multi-step reaction with 6 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

With dmap; manganese(IV) oxide; 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; dichloromethane;
DOI:10.1021/ja9607796

Reference yield:

: 100-39-0
benzyl bromide

: 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

Guidance literature:: Multi-step reaction with 2 steps

1: 82 percent / DBU / acetonitrile / Ambient temperature

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

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