Tetradecanoic acid, 3-hydroxy-, ethyl ester, (3S)-

Base Information

• Chemical Name: Tetradecanoic acid, 3-hydroxy-, ethyl ester, (3S)-
• CAS No.: 477587-43-2
• Molecular Formula: C16H32O3
• Mol file: 477587-43-2.mol

Synonyms:

Chemical Property of Tetradecanoic acid, 3-hydroxy-, ethyl ester, (3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Tetradecanoic acid, 3-hydroxy-, ethyl ester, (3S)-

There total 1 articles about Tetradecanoic acid, 3-hydroxy-, ethyl ester, (3S)- 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:

ethyl 3-oxotetradecanoate (74124-22-4) → (R)-3-hydroxytetradecanoic acid ethyl ester (151763-75-6) + (S)-ethyl 3-hydroxytetradecanoate (477587-43-2)

Guidance literature:

With chiral diphenylphosphine-based reagent; hydrogen; In ethanol; at 50 ℃; under 37503.8 Torr; Title compound not separated from byproducts.;

DOI:10.1080/00397910701196538

Reference yield:

(S)-ethyl 3-hydroxytetradecanoate (477587-43-2) → N6-benzyloxycarbonyl-N2-tert-butoxycarbonyl-lysyl-γ-methyl-leucyl-[(2R,3R)-2-methyl-3-undecyl-β-alanyl]-glycine ethyl ester (269411-10-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: LiOH / tetrahydrofuran; methanol; H₂O

2.1: 96 percent / benzotriazol-1-yloxy-tris(dimethylamino)phosphonium chloride; ethyldiisopropylamine / CH₂Cl₂

3.1: 46 percent / diethyl azodicarboxylate; triphenylphosphane / tetrahydrofuran

4.1: LiHMDS / tetrahydrofuran

4.2: 93 percent / tetrahydrofuran

5.1: ammonium cerium(IV) nitrate / acetonitrile; H₂O

6.1: 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂

7.1: sodium hydroxide / tetrahydrofuran; H₂O

8.1: 91 percent / WSCD*HCl; benzotriazol-1-ol hydrate; triethylamine / dimethylformamide

9.1: trifluoroacetic acid / CH₂Cl₂

10.1: WSCD*HCl; benzotriazol-1-ol hydrate; triethylamine / tetrahydrofuran

11.1: trifluoroacetic acid / CH₂Cl₂

12.1: WSCD*HCl; benzotriazol-1-ol hydrate; triethylamine / tetrahydrofuran

With dmap; lithium hydroxide; sodium hydroxide; ammonium cerium(IV) nitrate; WSCD*HCl; benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium chloride; 1-hydroxybenzotriazol-hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Hydrolysis / 2.1: Acylation / 3.1: Cyclization / 4.1: Metallation / 4.2: Methylation / 5.1: dearylation / 6.1: Acylation / 7.1: Hydrolysis / 8.1: Acylation / 9.1: Hydrolysis / 10.1: Acylation / 11.1: Hydrolysis / 12.1: Acylation;

DOI:10.1021/ol005630k

Reference yield:

(S)-ethyl 3-hydroxytetradecanoate (477587-43-2) → (R)-1-(4-Methoxy-phenyl)-4-undecyl-azetidin-2-one (172941-53-6)

Guidance literature:

Multi-step reaction with 3 steps

1: LiOH / tetrahydrofuran; methanol; H₂O

2: 96 percent / benzotriazol-1-yloxy-tris(dimethylamino)phosphonium chloride; ethyldiisopropylamine / CH₂Cl₂

3: 46 percent / diethyl azodicarboxylate; triphenylphosphane / tetrahydrofuran

With lithium hydroxide; benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium chloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; 1: Hydrolysis / 2: Acylation / 3: Cyclization;

DOI:10.1021/ol005630k

upstream raw materials:

ethyl 3-oxotetradecanoate

Downstream raw materials:

(3S)-3-hydroxytetradecanoic acid

(R)-1-(4-Methoxy-phenyl)-4-undecyl-azetidin-2-one

(3R,4R)-1-(4-methoxy-phenyl)-3-methyl-4-undecyl-azetidine-2-one

(S)-3-Hydroxy-tetradecanoic acid (4-methoxy-phenyl)-amide