(E)-(5S,6R,8R,10S)-11-Benzyloxy-5-hydroxy-2,6,8,10-tetramethyl-undec-2-enoic acid ethyl ester

Base Information

Chemical Name:(E)-(5S,6R,8R,10S)-11-Benzyloxy-5-hydroxy-2,6,8,10-tetramethyl-undec-2-enoic acid ethyl ester
CAS No.:333354-19-1
Molecular Formula:C₂₄H₃₈O₄
Molecular Weight:390.563
Hs Code.:

Synonyms:(E)-(5S,6R,8R,10S)-11-Benzyloxy-5-hydroxy-2,6,8,10-tetramethyl-undec-2-enoic acid ethyl ester

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Chemical Property of (E)-(5S,6R,8R,10S)-11-Benzyloxy-5-hydroxy-2,6,8,10-tetramethyl-undec-2-enoic acid ethyl ester

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Technology Process of (E)-(5S,6R,8R,10S)-11-Benzyloxy-5-hydroxy-2,6,8,10-tetramethyl-undec-2-enoic acid ethyl ester

There total 10 articles about (E)-(5S,6R,8R,10S)-11-Benzyloxy-5-hydroxy-2,6,8,10-tetramethyl-undec-2-enoic 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: 90.0%

: (E)-3-[(2S,3R)-3-((1R,3R,5S)-6-Benzyloxy-1,3,5-trimethyl-hexyl)-oxiranyl]-2-methyl-acrylic acid ethyl ester

: 333354-19-1
(E)-(5S,6R,8R,10S)-11-Benzyloxy-5-hydroxy-2,6,8,10-tetramethyl-undec-2-enoic acid ethyl ester

Guidance literature:: With formic acid; tributylphosphine; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In 1,4-dioxane; at 23 ℃; for 10h;
DOI:10.1021/ol0100069

Reference yield:

: C₁₈H₂₇IO

: 333354-19-1
(E)-(5S,6R,8R,10S)-11-Benzyloxy-5-hydroxy-2,6,8,10-tetramethyl-undec-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.66 g / n-BuLi; TMEDA / diethyl ether / -78 °C

2: 747 mg / O₃; triphenylphosphine / CH₂Cl₂ / 4 h / 23 °C

3: NaH / tetrahydrofuran / 23 °C

4: 740 g / diisobutylaluminium hydride / CH₂Cl₂; various solvent(s) / -40 °C

5: 90 percent / (-)-DET; Ti(OiPr)4; TBHP / CH₂Cl₂ / 20 h / -23 °C

6: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 °C

7: 0.6 percent / benzene / 15 h / 80 °C

8: 90 percent / n-Bu₃P; formic acid; triethylamine / Pd₂(dba)3*CHCl₃ / dioxane / 10 h / 23 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; formic acid; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; tributylphosphine; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; benzene; 3: Horner-Emmons olefination / 5: Sharpless asymmetric epoxidation / 6: Swern oxidation / 7: Wittig homologation;
DOI:10.1021/ol0100069

Reference yield:

: C₁₈H₂₈O₂

: 333354-19-1
(E)-(5S,6R,8R,10S)-11-Benzyloxy-5-hydroxy-2,6,8,10-tetramethyl-undec-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: iodine; triphenylphosphine; imidazole / CH₂Cl₂ / 23 °C

2: 1.66 g / n-BuLi; TMEDA / diethyl ether / -78 °C

3: 747 mg / O₃; triphenylphosphine / CH₂Cl₂ / 4 h / 23 °C

4: NaH / tetrahydrofuran / 23 °C

5: 740 g / diisobutylaluminium hydride / CH₂Cl₂; various solvent(s) / -40 °C

6: 90 percent / (-)-DET; Ti(OiPr)4; TBHP / CH₂Cl₂ / 20 h / -23 °C

7: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 °C

8: 0.6 percent / benzene / 15 h / 80 °C

9: 90 percent / n-Bu₃P; formic acid; triethylamine / Pd₂(dba)3*CHCl₃ / dioxane / 10 h / 23 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; formic acid; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; tributylphosphine; iodine; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; benzene; 4: Horner-Emmons olefination / 6: Sharpless asymmetric epoxidation / 7: Swern oxidation / 8: Wittig homologation;
DOI:10.1021/ol0100069