(E)-(R)-5-(2-Bromo-acetoxy)-hex-2-enoic acid (1S,4R)-5,5-diethoxy-4-(4-methoxy-phenoxy)-1-methyl-pentyl ester

Base Information

Chemical Name:(E)-(R)-5-(2-Bromo-acetoxy)-hex-2-enoic acid (1S,4R)-5,5-diethoxy-4-(4-methoxy-phenoxy)-1-methyl-pentyl ester
CAS No.:192992-71-5
Molecular Formula:C₂₅H₃₇BrO₈
Molecular Weight:545.468
Hs Code.:

Synonyms:(E)-(R)-5-(2-Bromo-acetoxy)-hex-2-enoic acid (1S,4R)-5,5-diethoxy-4-(4-methoxy-phenoxy)-1-methyl-pentyl ester

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Chemical Property of (E)-(R)-5-(2-Bromo-acetoxy)-hex-2-enoic acid (1S,4R)-5,5-diethoxy-4-(4-methoxy-phenoxy)-1-methyl-pentyl ester

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Technology Process of (E)-(R)-5-(2-Bromo-acetoxy)-hex-2-enoic acid (1S,4R)-5,5-diethoxy-4-(4-methoxy-phenoxy)-1-methyl-pentyl ester

There total 9 articles about (E)-(R)-5-(2-Bromo-acetoxy)-hex-2-enoic acid (1S,4R)-5,5-diethoxy-4-(4-methoxy-phenoxy)-1-methyl-pentyl 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: 90.0%

: 598-21-0
2-Bromoacetyl bromide

: 192992-67-9
(E)-(R)-5-Hydroxy-hex-2-enoic acid (1S,4R)-5,5-diethoxy-4-(4-methoxy-phenoxy)-1-methyl-pentyl ester

: 192992-71-5
(E)-(R)-5-(2-Bromo-acetoxy)-hex-2-enoic acid (1S,4R)-5,5-diethoxy-4-(4-methoxy-phenoxy)-1-methyl-pentyl ester

Guidance literature:: With pyridine; In dichloromethane; at -20 ℃; for 0.5h;
DOI:10.1021/jo970020s

Reference yield:

: 158782-81-1
(E)-(2S,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,1-diethoxy-hex-3-en-2-ol

: 192992-71-5
(E)-(R)-5-(2-Bromo-acetoxy)-hex-2-enoic acid (1S,4R)-5,5-diethoxy-4-(4-methoxy-phenoxy)-1-methyl-pentyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 68 percent / H₂ / Pd/C / ethyl acetate / 760 Torr / Ambient temperature

2: 85 percent / DEAD, Ph₃P / tetrahydrofuran / 3 h / 90 °C

3: 81 percent / tetrabutylammonium fluoride / tetrahydrofuran / 72 h / Ambient temperature

4: 86 percent / pyridine / 0.33 h / Ambient temperature

5: 94 percent / acetonitrile / 24 h / Ambient temperature

6: 74 percent / TEA / acetonitrile / 24 h / 40 °C

7: 73 percent / tetrabutylammonium fluoride, acetic acid / tetrahydrofuran / 96 h / Ambient temperature

8: 90 percent / pyridine / CH₂Cl₂ / 0.5 h / -20 °C

With pyridine; TEA; tetrabutyl ammonium fluoride; hydrogen; acetic acid; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/jo970020s

Reference yield:

: 158782-80-0
(E)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,1-diethoxy-hex-3-en-2-one

: 192992-71-5
(E)-(R)-5-(2-Bromo-acetoxy)-hex-2-enoic acid (1S,4R)-5,5-diethoxy-4-(4-methoxy-phenoxy)-1-methyl-pentyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: (S)-2-(hydroxydiphenylmethyl)pyrrolidine, bis(trifluoroethyl) n-butylboronate, BH₃*Me₂S / tetrahydrofuran / 0.5 h / 0 °C

2: 68 percent / H₂ / Pd/C / ethyl acetate / 760 Torr / Ambient temperature

3: 85 percent / DEAD, Ph₃P / tetrahydrofuran / 3 h / 90 °C

4: 81 percent / tetrabutylammonium fluoride / tetrahydrofuran / 72 h / Ambient temperature

5: 86 percent / pyridine / 0.33 h / Ambient temperature

6: 94 percent / acetonitrile / 24 h / Ambient temperature

7: 74 percent / TEA / acetonitrile / 24 h / 40 °C

8: 73 percent / tetrabutylammonium fluoride, acetic acid / tetrahydrofuran / 96 h / Ambient temperature

9: 90 percent / pyridine / CH₂Cl₂ / 0.5 h / -20 °C

With pyridine; (S)-diphenylprolinol; dimethylsulfide borane complex; bis(trifluoroethyl) n-butylboronate; TEA; tetrabutyl ammonium fluoride; hydrogen; acetic acid; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/jo970020s