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

Base Information

Chemical Name:(Z)-(4S,7R)-4,7-bis(2,2-dimethylpropionyloxy)-8-oxoocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
CAS No.:300578-96-5
Molecular Formula:C₃₄H₅₀O₇
Molecular Weight:570.767
Hs Code.:

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

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

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

There total 7 articles about (Z)-(4S,7R)-4,7-bis(2,2-dimethylpropionyloxy)-8-oxoocta-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: 71.0%

: 155795-46-3
[bis(2,2,2-trifluoroethoxy)phosphoryl]acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

: 300578-89-6
meso-(2R,5S)-2,5-bis(2,2-dimethylpropionyloxy)hexane-1,6-dial

: 300578-96-5
(Z)-(4S,7R)-4,7-bis(2,2-dimethylpropionyloxy)-8-oxoocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Guidance literature:: With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -85 ℃;
DOI:10.1021/ol006135r

Reference yield: 71.0%

: 155795-46-3
[bis(2,2,2-trifluoroethoxy)phosphoryl]acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

: 300578-89-6
meso-(2R,5S)-2,5-bis(2,2-dimethylpropionyloxy)hexane-1,6-dial

: 300578-96-5
(Z)-(4S,7R)-4,7-bis(2,2-dimethylpropionyloxy)-8-oxoocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

: (2E,8E)-(4S,7R)-4,7-Bis-(2,2-dimethyl-propionyloxy)-deca-2,8-dienedioic acid bis-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester

Guidance literature:: [bis(2,2,2-trifluoroethoxy)phosphoryl]acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

meso-(2R,5S)-2,5-bis(2,2-dimethylpropionyloxy)hexane-1,6-dial; In tetrahydrofuran; toluene; at -85 ℃; Further stages.;
DOI:10.1021/jo0259111

Reference yield:

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

: 300578-96-5
(Z)-(4S,7R)-4,7-bis(2,2-dimethylpropionyloxy)-8-oxoocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Guidance literature:: Multi-step reaction with 4 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: 71 percent / tetrahydrofuran; toluene / -85 °C

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