Decanoic acid, 2,3-dihydroxy-2,8-dimethyl-6-[(1R)-1-(phenylmethoxy)propyl]-, ethyl ester, (2S,3R,6R,8S)-

Base Information

• Chemical Name: Decanoic acid, 2,3-dihydroxy-2,8-dimethyl-6-[(1R)-1-(phenylmethoxy)propyl]-, ethyl ester, (2S,3R,6R,8S)-
• CAS No.: 873000-85-2
• Molecular Formula: C24H40O5
• Molecular Weight: 408.579
• Mol file: 873000-85-2.mol

Synonyms:

Chemical Property of Decanoic acid, 2,3-dihydroxy-2,8-dimethyl-6-[(1R)-1-(phenylmethoxy)propyl]-, ethyl ester, (2S,3R,6R,8S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Decanoic acid, 2,3-dihydroxy-2,8-dimethyl-6-[(1R)-1-(phenylmethoxy)propyl]-, ethyl ester, (2S,3R,6R,8S)-

There total 10 articles about Decanoic acid, 2,3-dihydroxy-2,8-dimethyl-6-[(1R)-1-(phenylmethoxy)propyl]-, ethyl ester, (2S,3R,6R,8S)- 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: 98.0%

(E)-(6R,8S)-6-((R)-1-Benzyloxy-propyl)-2,8-dimethyl-dec-2-enoic acid ethyl ester (873000-84-1) → (2S,3R,6R,8S)-6-((R)-1-Benzyloxy-propyl)-2,3-dihydroxy-2,8-dimethyl-decanoic acid ethyl ester (873000-85-2)

Guidance literature:

With AD-mix-β;

DOI:10.1055/s-2005-918924

Reference yield:

(E)-(S)-1-Bromo-5-methyl-hept-2-ene → (2S,3R,6R,8S)-6-((R)-1-Benzyloxy-propyl)-2,3-dihydroxy-2,8-dimethyl-decanoic acid ethyl ester (873000-85-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaH

2.1: n-BuLi; (-)-sparteine / hexane; toluene / 0.75 h / -78 °C

2.2: Et₂AlCl / hexane; toluene / 1 h / -78 °C

2.3: 82 percent / hexane; toluene / 12 h / -78 °C

3.1: NaH / tetrahydrofuran

4.1: aq. HCl / CHCl₃

5.1: LDA

6.1: aq. HCl / CHCl₃

7.1: 77 percent / t-BuOK / dimethylformamide

8.1: 98 percent / AD-mix-β

With hydrogenchloride; n-butyllithium; AD-mix-β; potassium tert-butylate; sodium hydride; (-)-sparteine; lithium diisopropyl amide; In tetrahydrofuran; hexane; chloroform; N,N-dimethyl-formamide; toluene; 5.1: Wittig olefination / 7.1: Horner-Wadsworth-Emmons reaction / 8.1: Sharpless asymmetric dihydroxylation;

DOI:10.1055/s-2005-918924

Reference yield:

(E)-(S)-5-Methyl-hept-2-en-1-ol (873000-77-2) → (2S,3R,6R,8S)-6-((R)-1-Benzyloxy-propyl)-2,3-dihydroxy-2,8-dimethyl-decanoic acid ethyl ester (873000-85-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NBS; Ph₃P / CH₂Cl₂

2.1: NaH

3.1: n-BuLi; (-)-sparteine / hexane; toluene / 0.75 h / -78 °C

3.2: Et₂AlCl / hexane; toluene / 1 h / -78 °C

3.3: 82 percent / hexane; toluene / 12 h / -78 °C

4.1: NaH / tetrahydrofuran

5.1: aq. HCl / CHCl₃

6.1: LDA

7.1: aq. HCl / CHCl₃

8.1: 77 percent / t-BuOK / dimethylformamide

9.1: 98 percent / AD-mix-β

With hydrogenchloride; N-Bromosuccinimide; n-butyllithium; AD-mix-β; potassium tert-butylate; sodium hydride; triphenylphosphine; (-)-sparteine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; 6.1: Wittig olefination / 8.1: Horner-Wadsworth-Emmons reaction / 9.1: Sharpless asymmetric dihydroxylation;

DOI:10.1055/s-2005-918924

upstream raw materials:

(E)-(6R,8S)-6-((R)-1-Benzyloxy-propyl)-2,8-dimethyl-dec-2-enoic acid ethyl ester

(E)-(S)-5-Methyl-hept-2-en-1-ol

(E)-(S)-5-Methyl-hept-2-enoic acid ethyl ester

(4R,6S)-4-((R)-1-Benzyloxy-propyl)-6-methyl-octanal

Downstream raw materials:

(2S,6R,8S)-6-((R)-1-Benzyloxy-propyl)-2-hydroxy-2,8-dimethyl-3-oxo-decanoic acid ethyl ester

Refernces