(E)-(4R,7S)-4,8-bis(2,2-dimethylpropionyloxy)-7-hydroxyocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Base Information

Chemical Name:(E)-(4R,7S)-4,8-bis(2,2-dimethylpropionyloxy)-7-hydroxyocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
CAS No.:300578-92-1
Molecular Formula:C₃₄H₅₂O₇
Molecular Weight:572.783
Hs Code.:

Synonyms:(E)-(4R,7S)-4,8-bis(2,2-dimethylpropionyloxy)-7-hydroxyocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

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Chemical Property of (E)-(4R,7S)-4,8-bis(2,2-dimethylpropionyloxy)-7-hydroxyocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

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Technology Process of (E)-(4R,7S)-4,8-bis(2,2-dimethylpropionyloxy)-7-hydroxyocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

There total 7 articles about (E)-(4R,7S)-4,8-bis(2,2-dimethylpropionyloxy)-7-hydroxyocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 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: 52.0%

: 300578-91-0
(E)-(4R,7S)-4,7-bis(2,2-dimethylpropionyloxy)-8-hydroxyocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

: 300578-92-1
(E)-(4R,7S)-4,8-bis(2,2-dimethylpropionyloxy)-7-hydroxyocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Guidance literature:: With dmap; In ethanol; at 75 ℃;
DOI:10.1021/jo0259111

Reference yield:

: 45620-68-6
cyclohex-2-ene-1,4-diol

: 300578-92-1
(E)-(4R,7S)-4,8-bis(2,2-dimethylpropionyloxy)-7-hydroxyocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 59 percent / 4-(dimethylamino)pyridine / pyridine / 3 h / Heating

2.1: 94 percent / RuCl₃ hydrate; NaIO₄ / acetonitrile; H₂O / 0.08 h / 0 °C

3.1: 99 percent / H₅IO₆ / tetrahydrofuran / 0 - 20 °C

4.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

4.2: 55 percent / tetrahydrofuran; toluene / -85 °C

5.1: 85 percent / NaBH₄ / methanol; tetrahydrofuran / 0 °C

6.1: 52 percent / 4-DMAP / ethanol / 75 °C

With dmap; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; 18-crown-6 ether; potassium hexamethylsilazane; periodic acid; In tetrahydrofuran; pyridine; methanol; ethanol; water; toluene; acetonitrile; 4.1: asymmetric Horner-Wadsworth-Emmons reaction / 4.2: asymmetric Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0259111

Reference yield:

: 113368-90-4
(Diisopropoxy-phosphoryl)-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

: 300578-92-1
(E)-(4R,7S)-4,8-bis(2,2-dimethylpropionyloxy)-7-hydroxyocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

1.2: 55 percent / tetrahydrofuran; toluene / -85 °C

2.1: 85 percent / NaBH₄ / methanol; tetrahydrofuran / 0 °C

3.1: 52 percent / 4-DMAP / ethanol / 75 °C

With dmap; sodium tetrahydroborate; 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; methanol; ethanol; toluene; 1.1: asymmetric Horner-Wadsworth-Emmons reaction / 1.2: asymmetric Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0259111