10-Undecenoic acid, 11-[(1S,2R,3R,5S)-3,5-bis(benzoyloxy)-2-ethylcyclopentyl]-9-oxo-, ethyl ester, (10E)-

Base Information

Chemical Name:10-Undecenoic acid, 11-[(1S,2R,3R,5S)-3,5-bis(benzoyloxy)-2-ethylcyclopentyl]-9-oxo-, ethyl ester, (10E)-
CAS No.:681449-46-7
Molecular Formula:C34H42O7
Molecular Weight:562.703
Hs Code.:

Synonyms:

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Chemical Property of 10-Undecenoic acid, 11-[(1S,2R,3R,5S)-3,5-bis(benzoyloxy)-2-ethylcyclopentyl]-9-oxo-, ethyl ester, (10E)-

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Technology Process of 10-Undecenoic acid, 11-[(1S,2R,3R,5S)-3,5-bis(benzoyloxy)-2-ethylcyclopentyl]-9-oxo-, ethyl ester, (10E)-

There total 8 articles about 10-Undecenoic acid, 11-[(1S,2R,3R,5S)-3,5-bis(benzoyloxy)-2-ethylcyclopentyl]-9-oxo-, ethyl ester, (10E)- 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: 79.0%

: 135062-25-8
dimethyl [9-(ethoxycarbonyl)-2-oxononyl]phosphonate

: 681449-45-6
C₂₂H₂₂O₅

: (1R,2R)-1-O-benzoyl-2-ethyl-3-[(E)-10-(ethoxycarbonyl)-3-oxodec-1-enyl]cyclopent-3-en-1-ol

: 681449-46-7
(1S,2S,3R,4R)-1,4-di-O-benzoyl-3-ethyl-2-[(E)-10-(ethoxycarbonyl)-3-oxodec-1-enyl]cyclopentane-1,4-diol

Guidance literature:: dimethyl [9-(ethoxycarbonyl)-2-oxononyl]phosphonate; With sodium hexamethyldisilazane; In tetrahydrofuran; toluene; at 20 ℃;

C₂₂H₂₂O₅; In tetrahydrofuran; toluene; at -78 - 20 ℃;
DOI:10.1021/jo035638i

Reference yield:

: 213777-18-5
(1S,2S,3R,4R)-1,4-Bis(triethylsilyloxy)-3-(methoxycarbonylmethyl)-2-tert-butyldiphenylsilyloxymethylcyclopentane

: 681449-46-7
(1S,2S,3R,4R)-1,4-di-O-benzoyl-3-ethyl-2-[(E)-10-(ethoxycarbonyl)-3-oxodec-1-enyl]cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 94 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / 1 h / -78 - 20 °C

2.1: 97 percent / DMAP; triethylamine / CH₂Cl₂ / 2 h / 20 °C

3.1: 91 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / Heating

4.1: 82 percent / ammonium fluoride / methanol; tetrahydrofuran / 2 h / Heating

5.1: 94 percent / pyridine / 1 h / 20 °C

6.1: 97 percent / acetyl chloride; methanol / diethyl ether / 20 h / 20 °C

7.1: Dess-Martin periodinane; water / CH₂Cl₂ / 3 h / 20 °C

8.1: NaHMDS / tetrahydrofuran; toluene / 20 °C

8.2: 79 percent / tetrahydrofuran; toluene / -78 - 20 °C

With pyridine; methanol; dmap; lithium aluminium tetrahydride; ammonium fluoride; water; sodium hexamethyldisilazane; Dess-Martin periodane; triethylamine; acetyl chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 7.1: Dess-Martin oxidation / 8.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo035638i

Reference yield:

: 681449-44-5
(1S,2R,3R,4R)-1,4-di-O-benzoyl-3-ethylcyclopentane-1,4-diol

: 681449-46-7
(1S,2S,3R,4R)-1,4-di-O-benzoyl-3-ethyl-2-[(E)-10-(ethoxycarbonyl)-3-oxodec-1-enyl]cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: Dess-Martin periodinane; water / CH₂Cl₂ / 3 h / 20 °C

2.1: NaHMDS / tetrahydrofuran; toluene / 20 °C

2.2: 79 percent / tetrahydrofuran; toluene / -78 - 20 °C

With water; sodium hexamethyldisilazane; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; toluene; 1.1: Dess-Martin oxidation / 2.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo035638i