(S)-3-((5S,12S)-17-hydroxy-12-(methoxymethoxy)-5-(3-phenylpropyl)-2,4,7,10-tetraoxatetracos-14-yn-24-yl)-5-methylfuran-2(5H)-one

Base Information

• Chemical Name: (S)-3-((5S,12S)-17-hydroxy-12-(methoxymethoxy)-5-(3-phenylpropyl)-2,4,7,10-tetraoxatetracos-14-yn-24-yl)-5-methylfuran-2(5H)-one
• CAS No.: 1261074-60-5
• Molecular Formula: C₃₆H₅₆O₉
• Molecular Weight: 632.835

Synonyms:(S)-3-((5S,12S)-17-hydroxy-12-(methoxymethoxy)-5-(3-phenylpropyl)-2,4,7,10-tetraoxatetracos-14-yn-24-yl)-5-methylfuran-2(5H)-one

Chemical Property of (S)-3-((5S,12S)-17-hydroxy-12-(methoxymethoxy)-5-(3-phenylpropyl)-2,4,7,10-tetraoxatetracos-14-yn-24-yl)-5-methylfuran-2(5H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (S)-3-((5S,12S)-17-hydroxy-12-(methoxymethoxy)-5-(3-phenylpropyl)-2,4,7,10-tetraoxatetracos-14-yn-24-yl)-5-methylfuran-2(5H)-one

There total 12 articles about (S)-3-((5S,12S)-17-hydroxy-12-(methoxymethoxy)-5-(3-phenylpropyl)-2,4,7,10-tetraoxatetracos-14-yn-24-yl)-5-methylfuran-2(5H)-one 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: 63.0%

(5S,12S)-5-(3-phenylpropyl)-12-(prop-2-ynyl)-2,4,7,10,13,15-hexaoxahexadecane (1261074-53-6) + (5S,8'RS)-3-(8',9'-Epoxynonanyl)-5-methyl-2,5-dihydrofuran-2-one (237752-79-3) → (S)-3-((5S,12S)-17-hydroxy-12-(methoxymethoxy)-5-(3-phenylpropyl)-2,4,7,10-tetraoxatetracos-14-yn-24-yl)-5-methylfuran-2(5H)-one (1261074-60-5)

Guidance literature:

(5S,12S)-5-(3-phenylpropyl)-12-(prop-2-ynyl)-2,4,7,10,13,15-hexaoxahexadecane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h; Inert atmosphere;

With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; for 0.5h; Inert atmosphere;

(5S,8'RS)-3-(8',9'-Epoxynonanyl)-5-methyl-2,5-dihydrofuran-2-one; In tetrahydrofuran; hexane; for 3h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jm101053k

Reference yield:

(S)-11-phenyl-5-(3-phenylprop-2-ynyl)-2,4,7,10-tetraoxaundecane (1261074-39-8) → (S)-3-((5S,12S)-17-hydroxy-12-(methoxymethoxy)-5-(3-phenylpropyl)-2,4,7,10-tetraoxatetracos-14-yn-24-yl)-5-methylfuran-2(5H)-one (1261074-60-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: palladium 10% on activated carbon; hydrogen; acetic acid / ethanol / 16 h / 20 °C

2.1: N-benzyl-N,N,N-triethylammonium chloride / 0.05 h

2.2: 22.25 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere

3.2: 0.5 h / Inert atmosphere

3.3: 3 h / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / Cooling

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere

6.2: 0.5 h / Inert atmosphere

6.3: 3 h / Inert atmosphere

With n-butyllithium; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane;

DOI:10.1021/jm101053k

Reference yield:

(S)-2-((S)-5-(3-phenylpropyl)-2,4,7,10-tetraoxaundecan-11-yl)-oxirane (1261074-46-7) → (S)-3-((5S,12S)-17-hydroxy-12-(methoxymethoxy)-5-(3-phenylpropyl)-2,4,7,10-tetraoxatetracos-14-yn-24-yl)-5-methylfuran-2(5H)-one (1261074-60-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere

1.2: 0.5 h / Inert atmosphere

1.3: 3 h / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / Cooling

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere

4.2: 0.5 h / Inert atmosphere

4.3: 3 h / Inert atmosphere

With n-butyllithium; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jm101053k

upstream raw materials:

(S)-11-phenyl-5-(3-phenylprop-2-ynyl)-2,4,7,10-tetraoxaundecane

(S)-2-((S)-5-(3-phenylpropyl)-2,4,7,10-tetraoxaundecan-11-yl)-oxirane

(5S,12S)-5-(3-phenylpropyl)-12-(prop-2-ynyl)-2,4,7,10,13,15-hexaoxahexadecane

(5S,8'RS)-3-(8',9'-Epoxynonanyl)-5-methyl-2,5-dihydrofuran-2-one

Downstream raw materials:

(S)-3-((13S)-8,13-dihydroxy-14-(2-(((S)-2-hydroxy-5-phenylpentyl)oxy)ethoxy)tetradecyl)-5-methylfuran-2(5H)-one

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