Acetic acid (1S,2S,4aR,4bS,6aS,11aS,11bR,13aR)-7,10-dihydroxy-1,4a,6a,11b-tetramethyl-1-[2-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-ethyl]-2,3,4,4a,4b,5,6,6a,11,11a,11b,12,13,13a-tetradecahydro-1H-indeno[2,1-a]phenanthren-2-yl ester

Base Information

• Chemical Name: Acetic acid (1S,2S,4aR,4bS,6aS,11aS,11bR,13aR)-7,10-dihydroxy-1,4a,6a,11b-tetramethyl-1-[2-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-ethyl]-2,3,4,4a,4b,5,6,6a,11,11a,11b,12,13,13a-tetradecahydro-1H-indeno[2,1-a]phenanthren-2-yl ester
• CAS No.: 259177-56-5
• Molecular Formula: C₃₈H₅₆O₄
• Molecular Weight: 576.86

Synonyms:Acetic acid (1S,2S,4aR,4bS,6aS,11aS,11bR,13aR)-7,10-dihydroxy-1,4a,6a,11b-tetramethyl-1-[2-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-ethyl]-2,3,4,4a,4b,5,6,6a,11,11a,11b,12,13,13a-tetradecahydro-1H-indeno[2,1-a]phenanthren-2-yl ester

Chemical Property of Acetic acid (1S,2S,4aR,4bS,6aS,11aS,11bR,13aR)-7,10-dihydroxy-1,4a,6a,11b-tetramethyl-1-[2-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-ethyl]-2,3,4,4a,4b,5,6,6a,11,11a,11b,12,13,13a-tetradecahydro-1H-indeno[2,1-a]phenanthren-2-yl ester

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Technology Process of Acetic acid (1S,2S,4aR,4bS,6aS,11aS,11bR,13aR)-7,10-dihydroxy-1,4a,6a,11b-tetramethyl-1-[2-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-ethyl]-2,3,4,4a,4b,5,6,6a,11,11a,11b,12,13,13a-tetradecahydro-1H-indeno[2,1-a]phenanthren-2-yl ester

There total 14 articles about Acetic acid (1S,2S,4aR,4bS,6aS,11aS,11bR,13aR)-7,10-dihydroxy-1,4a,6a,11b-tetramethyl-1-[2-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-ethyl]-2,3,4,4a,4b,5,6,6a,11,11a,11b,12,13,13a-tetradecahydro-1H-indeno[2,1-a]phenanthren-2-yl 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:

[(S)-2,6,6-trimethylcyclohex-2-enyl]methanol (52646-93-2) → Acetic acid (1S,2S,4aR,4bS,6aS,11aS,11bR,13aR)-7,10-dihydroxy-1,4a,6a,11b-tetramethyl-1-[2-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-ethyl]-2,3,4,4a,4b,5,6,6a,11,11a,11b,12,13,13a-tetradecahydro-1H-indeno[2,1-a]phenanthren-2-yl ester (259177-56-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: PPh₃,; I₂,; imidazole / benzene

2.1: tert-butyllithium

2.2: -78 °C

3.1: n-BuLi

4.1: AIBN,; (n-Bu)3SnH / 80 °C

5.1: (n-Bu)4NF

6.1: DMAP

7.1: (NH₄)2Ce(NO₃)6

With 1H-imidazole; dmap; n-butyllithium; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; tri-n-butyl-tin hydride; triphenylphosphine; In benzene; 1.1: Iodination / 2.1: Metallation / 2.2: Addition / 3.1: Metallation / 3.2: Addition / 3.3: Methylation / 4.1: Reduction / 5.1: desilylation / 6.1: Acetylation / 7.1: demethylation;

DOI:10.1021/ja9934091

Reference yield:

((1R,2S,4aR,4bS,6aS,11aS,11bR,13aR)-1-Benzyloxymethyl-7,10-dimethoxy-1,4a,6a,11b-tetramethyl-2,3,4,4a,4b,5,6,6a,11,11a,11b,12,13,13a-tetradecahydro-1H-indeno[2,1-a]phenanthren-2-yloxy)-tert-butyl-dimethyl-silane (259177-48-5) → Acetic acid (1S,2S,4aR,4bS,6aS,11aS,11bR,13aR)-7,10-dihydroxy-1,4a,6a,11b-tetramethyl-1-[2-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-ethyl]-2,3,4,4a,4b,5,6,6a,11,11a,11b,12,13,13a-tetradecahydro-1H-indeno[2,1-a]phenanthren-2-yl ester (259177-56-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: H₂ / Pd/C

2.1: 'Dess-Martin reagent

3.1: tert-butyllithium

3.2: -78 °C

4.1: n-BuLi

5.1: AIBN,; (n-Bu)3SnH / 80 °C

6.1: (n-Bu)4NF

7.1: DMAP

8.1: (NH₄)2Ce(NO₃)6

With dmap; n-butyllithium; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; tri-n-butyl-tin hydride; Dess-Martin periodane; palladium on activated charcoal; 1.1: Hydrogenolysis / 2.1: Oxidation / 3.1: Metallation / 3.2: Addition / 4.1: Metallation / 4.2: Addition / 4.3: Methylation / 5.1: Reduction / 6.1: desilylation / 7.1: Acetylation / 8.1: demethylation;

DOI:10.1021/ja9934091

Reference yield:

((1R,2S,4aR,4bS,6aS,11aS,11bR,13aR)-9-Allyloxy-1-benzyloxymethyl-7,10-dimethoxy-1,4a,6a,11b-tetramethyl-2,3,4,4a,4b,5,6,6a,11,11a,11b,12,13,13a-tetradecahydro-1H-indeno[2,1-a]phenanthren-2-yloxy)-tert-butyl-dimethyl-silane (259183-97-6) → Acetic acid (1S,2S,4aR,4bS,6aS,11aS,11bR,13aR)-7,10-dihydroxy-1,4a,6a,11b-tetramethyl-1-[2-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-ethyl]-2,3,4,4a,4b,5,6,6a,11,11a,11b,12,13,13a-tetradecahydro-1H-indeno[2,1-a]phenanthren-2-yl ester (259177-56-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: Pd(PPh₃)4,; pyrrolidine

2.1: Cs₂CO₃

3.1: Pd(dppp),; (n-Bu)3N,; HCO₂H

4.1: H₂ / Pd/C

5.1: 'Dess-Martin reagent

6.1: tert-butyllithium

6.2: -78 °C

7.1: n-BuLi

8.1: AIBN,; (n-Bu)3SnH / 80 °C

9.1: (n-Bu)4NF

10.1: DMAP

11.1: (NH₄)2Ce(NO₃)6

With pyrrolidine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; formic acid; ammonium cerium(IV) nitrate; tributyl-amine; 2,2'-azobis(isobutyronitrile); Pd(dppp); tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; tri-n-butyl-tin hydride; caesium carbonate; Dess-Martin periodane; palladium on activated charcoal; 1.1: deallylation / 2.1: triflation / 3.1: Reduction / 4.1: Hydrogenolysis / 5.1: Oxidation / 6.1: Metallation / 6.2: Addition / 7.1: Metallation / 7.2: Addition / 7.3: Methylation / 8.1: Reduction / 9.1: desilylation / 10.1: Acetylation / 11.1: demethylation;

DOI:10.1021/ja9934091

upstream raw materials:

Acetic acid (1S,2S,4aR,4bS,6aS,11aS,11bR,13aR)-7,10-dimethoxy-1,4a,6a,11b-tetramethyl-1-[2-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-ethyl]-2,3,4,4a,4b,5,6,6a,11,11a,11b,12,13,13a-tetradecahydro-1H-indeno[2,1-a]phenanthren-2-yl ester

[(S)-2,6,6-trimethylcyclohex-2-enyl]methanol

(S)-6-Iodomethyl-1,5,5-trimethyl-cyclohexene

(1S,2S,4aR,4bS,6aS,11aS,11bR,13aR)-2-(tert-Butyl-dimethyl-silanyloxy)-7,10-dimethoxy-1,4a,6a,11b-tetramethyl-2,3,4,4a,4b,5,6,6a,11,11a,11b,12,13,13a-tetradecahydro-1H-indeno[2,1-a]phenanthrene-1-carbaldehyde

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