(4E,6Z)-6-Bromo-7-{(4S,5R)-5-[(3E,5E)-(1S,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-1,5,7-trimethyl-2-oxo-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)-8-hydroxy-1,5,7-trimethyl-2-oxo-deca-3,5-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-4,6-dienoic acid
CAS No.:179943-83-0
Molecular Formula:C₄₁H₅₅BrO₇Si
Molecular Weight:767.873
Hs Code.:

(4E,6Z)-6-Bromo-7-{(4S,5R)-5-[(3E,5E)-(1S,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-1,5,7-trimethyl-2-oxo-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)-8-hydroxy-1,5,7-trimethyl-2-oxo-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)-8-hydroxy-1,5,7-trimethyl-2-oxo-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)-8-hydroxy-1,5,7-trimethyl-2-oxo-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)-8-hydroxy-1,5,7-trimethyl-2-oxo-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: 90.0%

: 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

: 179943-83-0
(4E,6Z)-6-Bromo-7-{(4S,5R)-5-[(3E,5E)-(1S,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-1,5,7-trimethyl-2-oxo-deca-3,5-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-4,6-dienoic acid

Guidance literature:: With hydrogen fluoride; In acetonitrile; for 5h;
DOI:10.1021/ja9607796

Reference yield:

: 6089-09-4
4-pentynoic acid

: 179943-83-0
(4E,6Z)-6-Bromo-7-{(4S,5R)-5-[(3E,5E)-(1S,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-1,5,7-trimethyl-2-oxo-deca-3,5-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-4,6-dienoic acid

Guidance literature:: Multi-step reaction with 4 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

4: 90 percent / 1 M aq. HF / acetonitrile / 5 h

With lithium hydroxide; TlOH; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; hydrogen fluoride; 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:

: 126378-11-8
4-pentynoic acid benzyl ester

: 179943-83-0
(4E,6Z)-6-Bromo-7-{(4S,5R)-5-[(3E,5E)-(1S,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-1,5,7-trimethyl-2-oxo-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: 1.) catecholborane, 2.) aq. NaCl, 3.) aq. TlOH, Pd₂(dba)3, Ph₃P

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

3: 90 percent / 1 M aq. HF / acetonitrile / 5 h

With lithium hydroxide; TlOH; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; hydrogen fluoride; triphenylphosphine; sodium chloride; benzo[1,3,2]dioxaborole; In 1,2-dimethoxyethane; acetonitrile;
DOI:10.1021/ja9607796