(3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoic acid

Base Information

• Chemical Name: (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoic acid
• CAS No.: 1585180-73-9
• Molecular Formula: C₂₂H₃₆O₅
• Molecular Weight: 380.525

Synonyms:(3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoic acid

Chemical Property of (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoic acid

There total 13 articles about (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoic 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:

(S)-5,5-dimethyl-4-hydroxyhexan-2-one (197454-20-9) → (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoic acid (1585180-73-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / methanol / 0.67 h / 0 °C / Inert atmosphere

3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 2.5 h / 0 °C / Inert atmosphere

4.1: potassium tert-butylate / toluene / 1 h / Reflux; Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Molecular sieve

6.1: triethylamine / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere

7.1: titanium(IV) isopropylate / dichloromethane / 1 h / Inert atmosphere; Reflux

7.2: 4 h / Inert atmosphere; Reflux

8.1: copper(l) cyanide / diethyl ether / 2.33 h / -78 °C / Inert atmosphere

8.2: 2.33 h / -78 - -20 °C

9.1: trimethylaluminum / dichloromethane; Hexachlorobutadiene / -78 - 20 °C / Inert atmosphere

10.1: trifluorormethanesulfonic acid / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

11.1: diisobutylaluminium hydride / toluene; tetrahydrofuran / -78 °C / Inert atmosphere

12.1: N-((4-methylphenyl)sulfonyl)-D-valine; borane; C₁₂H₁₆BNO₄S / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

13.1: lithium hydroxide; water / methanol; tetrahydrofuran / 5 h / 20 °C / Inert atmosphere

With 1H-imidazole; titanium(IV) isopropylate; sodium tetrahydroborate; trifluorormethanesulfonic acid; C₁₂H₁₆BNO₄S; N-((4-methylphenyl)sulfonyl)-D-valine; borane; potassium tert-butylate; tetrabutyl ammonium fluoride; water; trimethylaluminum; copper(l) cyanide; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; lithium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; Hexachlorobutadiene; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm4019965

Reference yield:

pivalaldehyde (630-19-3) → (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoic acid (1585180-73-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: D-Prolin / acetone; dimethyl sulfoxide / 97 h / 20 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

3.1: sodium tetrahydroborate / methanol / 0.67 h / 0 °C / Inert atmosphere

4.1: triethylamine; methanesulfonyl chloride / dichloromethane / 2.5 h / 0 °C / Inert atmosphere

5.1: potassium tert-butylate / toluene / 1 h / Reflux; Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Molecular sieve

7.1: triethylamine / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere

8.1: titanium(IV) isopropylate / dichloromethane / 1 h / Inert atmosphere; Reflux

8.2: 4 h / Inert atmosphere; Reflux

9.1: copper(l) cyanide / diethyl ether / 2.33 h / -78 °C / Inert atmosphere

9.2: 2.33 h / -78 - -20 °C

10.1: trimethylaluminum / dichloromethane; Hexachlorobutadiene / -78 - 20 °C / Inert atmosphere

11.1: trifluorormethanesulfonic acid / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

12.1: diisobutylaluminium hydride / toluene; tetrahydrofuran / -78 °C / Inert atmosphere

13.1: N-((4-methylphenyl)sulfonyl)-D-valine; borane; C₁₂H₁₆BNO₄S / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

14.1: lithium hydroxide; water / methanol; tetrahydrofuran / 5 h / 20 °C / Inert atmosphere

With 1H-imidazole; titanium(IV) isopropylate; sodium tetrahydroborate; trifluorormethanesulfonic acid; C₁₂H₁₆BNO₄S; N-((4-methylphenyl)sulfonyl)-D-valine; borane; potassium tert-butylate; tetrabutyl ammonium fluoride; water; trimethylaluminum; copper(l) cyanide; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; D-Prolin; lithium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; Hexachlorobutadiene; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jm4019965

Reference yield:

4-(tert-butyl-dimethyl-silanyloxy)-5,5-dimethyl-hexan-2-ol → (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoic acid (1585180-73-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: triethylamine; methanesulfonyl chloride / dichloromethane / 2.5 h / 0 °C / Inert atmosphere

2.1: potassium tert-butylate / toluene / 1 h / Reflux; Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Molecular sieve

4.1: triethylamine / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere

5.1: titanium(IV) isopropylate / dichloromethane / 1 h / Inert atmosphere; Reflux

5.2: 4 h / Inert atmosphere; Reflux

6.1: copper(l) cyanide / diethyl ether / 2.33 h / -78 °C / Inert atmosphere

6.2: 2.33 h / -78 - -20 °C

7.1: trimethylaluminum / dichloromethane; Hexachlorobutadiene / -78 - 20 °C / Inert atmosphere

8.1: trifluorormethanesulfonic acid / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / toluene; tetrahydrofuran / -78 °C / Inert atmosphere

10.1: N-((4-methylphenyl)sulfonyl)-D-valine; borane; C₁₂H₁₆BNO₄S / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

11.1: lithium hydroxide; water / methanol; tetrahydrofuran / 5 h / 20 °C / Inert atmosphere

With titanium(IV) isopropylate; trifluorormethanesulfonic acid; C₁₂H₁₆BNO₄S; N-((4-methylphenyl)sulfonyl)-D-valine; borane; potassium tert-butylate; tetrabutyl ammonium fluoride; water; trimethylaluminum; copper(l) cyanide; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; lithium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; Hexachlorobutadiene; toluene;

DOI:10.1021/jm4019965

upstream raw materials:

(S)-5,5-dimethyl-4-hydroxyhexan-2-one

pivalaldehyde

(3S)-2,2-dimethyl-5-hexen-3-ol

(S)-5,5-dimethyl-4-(tert-butyldimethylsilyloxy)hexan-2-one

Downstream raw materials:

allyl (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoate

pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3,6-dimethyl-5-(2,2,2-trichloroethoxycarbonyloxy)-hept-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester

apratoxin S₁₀

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