5-[1-(4-bromo-phenyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-pentyloxy]-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid

Base Information

Chemical Name:5-[1-(4-bromo-phenyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-pentyloxy]-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid
CAS No.:1026938-43-1
Molecular Formula:C₃₄H₆₅BrO₆Si₃
Molecular Weight:734.047
Hs Code.:

5-[1-(4-bromo-phenyl)-3,5-bis-(<i>tert</i>-butyl-dimethyl-silanyloxy)-pentyloxy]-3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-pentanoic acid

Synonyms:5-[1-(4-bromo-phenyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-pentyloxy]-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid

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Chemical Property of 5-[1-(4-bromo-phenyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-pentyloxy]-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid

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Technology Process of 5-[1-(4-bromo-phenyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-pentyloxy]-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid

There total 7 articles about 5-[1-(4-bromo-phenyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-pentyloxy]-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic 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: 81.0%

: 913626-28-5
(R)-5-[(1S,3S)-1-(4-Bromo-phenyl)-3,5-dihydroxy-pentyloxy]-3-hydroxy-pentanoic acid tert-butyl ester

: 69739-34-0
t-butyldimethylsiyl triflate

: 1026938-43-1
5-[1-(4-bromo-phenyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-pentyloxy]-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -30 - 25 ℃; for 23.67h;
DOI:10.1021/ol0618149

Reference yield:

: 913626-19-4
3-[(1S)-1-(4-bromo-phenyl)-but-3-enyloxy]-propionitrile

: 1026938-43-1
5-[1-(4-bromo-phenyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-pentyloxy]-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: 96 percent / zinc / Cp₂TiCl₂ / tetrahydrofuran / 4 h / 60 °C

2.1: ozone / CH₂Cl₂ / 0.08 h / -78 °C

2.2: triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

3.1: 1.8219 g / SnCl₄ / CH₂Cl₂ / 3.33 h / -78 - 25 °C

4.1: NaBH₄ / methanol / 0.33 h / 0 °C

5.1: 70 percent / lithium triethylborohydride / tetrahydrofuran / 1.75 h / 0 - 25 °C

6.1: 81 percent / 2,6-lutidine / CH₂Cl₂ / 23.67 h / -30 - 25 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; tin(IV) chloride; lithium triethylborohydride; ozone; zinc; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; methanol; dichloromethane; 1.1: Blaise reaction / 3.1: Roskamp homologation;
DOI:10.1021/ol0618149

Reference yield:

: 221898-37-9
(S)-1-(4-bromophenyl)but-3-en-1-ol

: 1026938-43-1
5-[1-(4-bromo-phenyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-pentyloxy]-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: 599 mg / Triton B / CH₂Cl₂; H₂O / 2 h / 20 - 25 °C

2.1: 96 percent / zinc / Cp₂TiCl₂ / tetrahydrofuran / 4 h / 60 °C

3.1: ozone / CH₂Cl₂ / 0.08 h / -78 °C

3.2: triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

4.1: 1.8219 g / SnCl₄ / CH₂Cl₂ / 3.33 h / -78 - 25 °C

5.1: NaBH₄ / methanol / 0.33 h / 0 °C

6.1: 70 percent / lithium triethylborohydride / tetrahydrofuran / 1.75 h / 0 - 25 °C

7.1: 81 percent / 2,6-lutidine / CH₂Cl₂ / 23.67 h / -30 - 25 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; tin(IV) chloride; N-benzyl-trimethylammonium hydroxide; lithium triethylborohydride; ozone; zinc; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; methanol; dichloromethane; water; 2.1: Blaise reaction / 4.1: Roskamp homologation;
DOI:10.1021/ol0618149