(3R,5S)-5-(4-Bromo-phenyl)-5-((R)-4-tert-butoxycarbonyl-3-hydroxy-butoxy)-3-hydroxy-pentanoic acid ethyl ester

Base Information

• Chemical Name: (3R,5S)-5-(4-Bromo-phenyl)-5-((R)-4-tert-butoxycarbonyl-3-hydroxy-butoxy)-3-hydroxy-pentanoic acid ethyl ester
• CAS No.: 913626-22-9
• Molecular Formula: C₂₂H₃₃BrO₇
• Molecular Weight: 489.404
• Mol file: 913626-22-9.mol

Synonyms:(3R,5S)-5-(4-Bromo-phenyl)-5-((R)-4-tert-butoxycarbonyl-3-hydroxy-butoxy)-3-hydroxy-pentanoic acid ethyl ester

Chemical Property of (3R,5S)-5-(4-Bromo-phenyl)-5-((R)-4-tert-butoxycarbonyl-3-hydroxy-butoxy)-3-hydroxy-pentanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S)-5-(4-Bromo-phenyl)-5-((R)-4-tert-butoxycarbonyl-3-hydroxy-butoxy)-3-hydroxy-pentanoic acid ethyl ester

There total 6 articles about (3R,5S)-5-(4-Bromo-phenyl)-5-((R)-4-tert-butoxycarbonyl-3-hydroxy-butoxy)-3-hydroxy-pentanoic acid ethyl 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: 89.0%

5-(4-bromo-phenyl)-5-(4-tert-butoxycarbonyl-3-oxo-butoxy)-3-oxo-pentanoic acid ethyl ester (913626-21-8) → (3S,5S)-5-(4-Bromo-phenyl)-5-((S)-4-tert-butoxycarbonyl-3-hydroxy-butoxy)-3-hydroxy-pentanoic acid ethyl ester + (3S,5S)-5-(4-Bromo-phenyl)-5-((R)-4-tert-butoxycarbonyl-3-hydroxy-butoxy)-3-hydroxy-pentanoic acid ethyl ester + (3R,5S)-5-(4-Bromo-phenyl)-5-((S)-4-tert-butoxycarbonyl-3-hydroxy-butoxy)-3-hydroxy-pentanoic acid ethyl ester + (3R,5S)-5-(4-Bromo-phenyl)-5-((R)-4-tert-butoxycarbonyl-3-hydroxy-butoxy)-3-hydroxy-pentanoic acid ethyl ester (913626-22-9)

Guidance literature:

With hydrogen; [(R)-BINAP]RuBr₂; In ethanol; at 45 ℃; for 72h; under 30002.4 Torr;

DOI:10.1021/ol0618149

Reference yield:

3-[(1S)-1-(4-bromo-phenyl)-but-3-enyloxy]-propionitrile (913626-19-4) → (3R,5S)-5-(4-Bromo-phenyl)-5-((R)-4-tert-butoxycarbonyl-3-hydroxy-butoxy)-3-hydroxy-pentanoic acid ethyl ester (913626-22-9)

Guidance literature:

Multi-step reaction with 4 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

With sodium tetrahydroborate; tin(IV) chloride; ozone; zinc; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; methanol; dichloromethane; 1.1: Blaise reaction / 3.1: Roskamp homologation;

DOI:10.1021/ol0618149

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → (3R,5S)-5-(4-Bromo-phenyl)-5-((R)-4-tert-butoxycarbonyl-3-hydroxy-butoxy)-3-hydroxy-pentanoic acid ethyl ester (913626-22-9)

Guidance literature:

Multi-step reaction with 4 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

With sodium tetrahydroborate; tin(IV) chloride; ozone; zinc; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; methanol; dichloromethane; 1.1: Blaise reaction / 3.1: Roskamp homologation;

DOI:10.1021/ol0618149

upstream raw materials:

5-(4-bromo-phenyl)-5-(4-tert-butoxycarbonyl-3-oxo-butoxy)-3-oxo-pentanoic acid ethyl ester

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

5-[1-(4-bromo-phenyl)-but-3-enyloxy]-3-oxo-pentanoic acid tert-butyl ester

bromoacetic acid tert-butyl ester

Downstream raw materials:

C₆₅H₁₁₇BrO₁₄Si₄

Octanoic acid (E)-(1S,5S,9S,11S,15R,19R,21S,24S)-11-(4-bromo-phenyl)-1,15-dihydroxy-19-hydroxymethyl-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-17-oxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.1^5,9]hexacos-3-en-24-yl ester

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

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