(S)-4-Bromo-3-hydroxy-4-pentenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester

Base Information

Chemical Name:(S)-4-Bromo-3-hydroxy-4-pentenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester
CAS No.:147986-42-3
Molecular Formula:C₂₅H₂₃BrO₄
Molecular Weight:467.359
Hs Code.:

Synonyms:(S)-4-Bromo-3-hydroxy-4-pentenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester

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Chemical Property of (S)-4-Bromo-3-hydroxy-4-pentenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (S)-4-Bromo-3-hydroxy-4-pentenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester

There total 1 articles about (S)-4-Bromo-3-hydroxy-4-pentenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl 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:

: 14925-39-4
2-bromoacrolein

: 95061-51-1
(S)-2-acetoxy-1,1,2-triphenylethanol

: 147986-42-3
(S)-4-Bromo-3-hydroxy-4-pentenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester

Guidance literature:: With magnesium bromide; lithium diisopropyl amide; Yield given. Multistep reaction; 1) a) THF, - 78 deg C, b) - 78 deg C to 0 deg C, 2) a) - 78 deg C, 1 h, b) - 115 deg C, 40 min;
DOI:10.1021/jo00061a028

Reference yield: 57.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 147986-42-3
(S)-4-Bromo-3-hydroxy-4-pentenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester

: (S)-4-Bromo-3-<(tret-butyldimethylsilyl)oxy>-4-pentenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester

Guidance literature:: With 1H-imidazole; In acetonitrile; for 3h; Ambient temperature;
DOI:10.1021/jo00061a028

Reference yield:

: 147986-42-3
(S)-4-Bromo-3-hydroxy-4-pentenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester

: <3S-(1Z,3α,5α)>-<3,5-Bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>acetic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 57 percent / imidazole / acetonitrile / 3 h / Ambient temperature

2: 89 percent / DIBAH / diethyl ether / 1 h / 0 °C

3: 84 percent / PCC, Zeolite 3 Angstroem / CH₂Cl₂ / 1 h / Ambient temperature

4: 1) LDA, 2) MgBr₂ / 1) a) THF, - 78 deg C, b) - 78 to 0 deg C, 2) a) - 78 deg C, b) - 115 deg C

5: 98 percent / imidazole / dimethylformamide / Ambient temperature

6: 83 percent / DIBAH / diethyl ether / 0 °C

7: 82 percent / PCC, Zeolite 3 Angstroem / CH₂Cl₂ / 1 h / Ambient temperature

8: 1) 18-crown-6, (TMS)2NK / 1) THF, -78 deg C, 20 min, 2) THF, 30 min

9: 5 percent / K₂CO₃ / Pd(OAc)2, PPh₃ / acetonitrile / Heating

With 1H-imidazole; 18-crown-6 ether; Zeolite 3 Angstroem; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; pyridinium chlorochromate; magnesium bromide; lithium diisopropyl amide; palladium diacetate; triphenylphosphine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00061a028