7-Cyclotetradecene-1-carboxylic acid, 7,11-dimethyl-4-(1-methylethyl)-3,13-dioxo-2-[(R)-phenylsulfinyl]-, methyl ester, (1R,2S,4S,7E,11S)-

Base Information

• Chemical Name: 7-Cyclotetradecene-1-carboxylic acid, 7,11-dimethyl-4-(1-methylethyl)-3,13-dioxo-2-[(R)-phenylsulfinyl]-, methyl ester, (1R,2S,4S,7E,11S)-
• CAS No.: 646519-72-4
• Molecular Formula: C₂₇H₃₈O₅S
• Molecular Weight: 474.662
• Mol file: 646519-72-4.mol

Synonyms:

Chemical Property of 7-Cyclotetradecene-1-carboxylic acid, 7,11-dimethyl-4-(1-methylethyl)-3,13-dioxo-2-[(R)-phenylsulfinyl]-, methyl ester, (1R,2S,4S,7E,11S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 7-Cyclotetradecene-1-carboxylic acid, 7,11-dimethyl-4-(1-methylethyl)-3,13-dioxo-2-[(R)-phenylsulfinyl]-, methyl ester, (1R,2S,4S,7E,11S)-

There total 17 articles about 7-Cyclotetradecene-1-carboxylic acid, 7,11-dimethyl-4-(1-methylethyl)-3,13-dioxo-2-[(R)-phenylsulfinyl]-, methyl ester, (1R,2S,4S,7E,11S)- 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)-3,7-dimethyl-6-octen-1-ol (7540-51-4) → (E)-(1R,2S,4S,11S)-2-((R)-Benzenesulfinyl)-4-isopropyl-7,11-dimethyl-3,13-dioxo-cyclotetradec-7-enecarboxylic acid methyl ester (646519-72-4)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 100 percent / pyridine / CH₂Cl₂ / 20 °C

2.1: 43 percent / selenium oxide; salicylic acid; tert-butyl hydroperoxide / CH₂Cl₂ / 30 h / 20 °C

3.1: Et₃N / tetrahydrofuran / 0 °C

4.1: 13.123 g / LiBr / tetrahydrofuran / 1 h / 20 °C

5.1: n-BuLi / hexane; tetrahydrofuran / 2 h / -25 °C

5.2: 92 percent / tetrahydrofuran; hexane / 2 h / 20 °C

6.1: 70 percent / Na₂HPO₄; Na-amalgam / tetrahydrofuran; methanol / 4 h / 20 °C

7.1: 81 percent / aq. HCl / propan-2-ol / 8 h / 55 °C

8.1: 86.4 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 4 h / 20 °C

9.1: LDA / tetrahydrofuran / 1 h / 0 °C

9.2: tetrahydrofuran / 1.75 h / -78 °C

9.3: 99 percent / NaOMe / methanol / 48 h / 30 °C

10.1: 83.3 percent / Dess-Martin periodinane / CH₂Cl₂ / 6 h / 10 °C

11.1: LDA / tetrahydrofuran / 0.17 h / -80 °C

11.2: 84.4 percent / tetrahydrofuran / 0.33 h / -80 °C

12.1: 100 percent / H₂; cyclohexane / Lindlar catalyst / CH₂Cl₂ / 1 h / 20 °C

13.1: 83.5 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

14.1: 85 percent / I₂ / diethyl ether / 2 h / 20 °C

15.1: Cs₂CO₃ / acetone / 7 h / 15 °C

With pyridine; hydrogenchloride; tert.-butylhydroperoxide; disodium hydrogenphosphate; n-butyllithium; selenium(IV) oxide; tetrapropylammonium perruthennate; sodium amalgam; cyclohexane; 4 A molecular sieve; hydrogen; iodine; caesium carbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; salicylic acid; lithium bromide; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; isopropyl alcohol; acetone; 15.1: intramolecular Michael reaction;

DOI:10.1021/jo035193y

Reference yield:

2,2-dimethyl-propionic acid (3S)-3,7-dimethyl-oct-6-enyl ester (93041-00-0) → (E)-(1R,2S,4S,11S)-2-((R)-Benzenesulfinyl)-4-isopropyl-7,11-dimethyl-3,13-dioxo-cyclotetradec-7-enecarboxylic acid methyl ester (646519-72-4)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 43 percent / selenium oxide; salicylic acid; tert-butyl hydroperoxide / CH₂Cl₂ / 30 h / 20 °C

2.1: Et₃N / tetrahydrofuran / 0 °C

3.1: 13.123 g / LiBr / tetrahydrofuran / 1 h / 20 °C

4.1: n-BuLi / hexane; tetrahydrofuran / 2 h / -25 °C

4.2: 92 percent / tetrahydrofuran; hexane / 2 h / 20 °C

5.1: 70 percent / Na₂HPO₄; Na-amalgam / tetrahydrofuran; methanol / 4 h / 20 °C

6.1: 81 percent / aq. HCl / propan-2-ol / 8 h / 55 °C

7.1: 86.4 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 4 h / 20 °C

8.1: LDA / tetrahydrofuran / 1 h / 0 °C

8.2: tetrahydrofuran / 1.75 h / -78 °C

8.3: 99 percent / NaOMe / methanol / 48 h / 30 °C

9.1: 83.3 percent / Dess-Martin periodinane / CH₂Cl₂ / 6 h / 10 °C

10.1: LDA / tetrahydrofuran / 0.17 h / -80 °C

10.2: 84.4 percent / tetrahydrofuran / 0.33 h / -80 °C

11.1: 100 percent / H₂; cyclohexane / Lindlar catalyst / CH₂Cl₂ / 1 h / 20 °C

12.1: 83.5 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

13.1: 85 percent / I₂ / diethyl ether / 2 h / 20 °C

14.1: Cs₂CO₃ / acetone / 7 h / 15 °C

With pyridine; hydrogenchloride; tert.-butylhydroperoxide; disodium hydrogenphosphate; n-butyllithium; selenium(IV) oxide; tetrapropylammonium perruthennate; sodium amalgam; cyclohexane; 4 A molecular sieve; hydrogen; iodine; caesium carbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; salicylic acid; lithium bromide; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; isopropyl alcohol; acetone; 14.1: intramolecular Michael reaction;

DOI:10.1021/jo035193y

Reference yield:

(S)-3-methyl-2-((phenylsulfonyl)methyl)butan-1-ol (152549-60-5) → (E)-(1R,2S,4S,11S)-2-((R)-Benzenesulfinyl)-4-isopropyl-7,11-dimethyl-3,13-dioxo-cyclotetradec-7-enecarboxylic acid methyl ester (646519-72-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 94.7 percent / diisopropylethyl amine / CH₂Cl₂ / 18 h / 20 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 2 h / -25 °C

2.2: 92 percent / tetrahydrofuran; hexane / 2 h / 20 °C

3.1: 70 percent / Na₂HPO₄; Na-amalgam / tetrahydrofuran; methanol / 4 h / 20 °C

4.1: 81 percent / aq. HCl / propan-2-ol / 8 h / 55 °C

5.1: 86.4 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 4 h / 20 °C

6.1: LDA / tetrahydrofuran / 1 h / 0 °C

6.2: tetrahydrofuran / 1.75 h / -78 °C

6.3: 99 percent / NaOMe / methanol / 48 h / 30 °C

7.1: 83.3 percent / Dess-Martin periodinane / CH₂Cl₂ / 6 h / 10 °C

8.1: LDA / tetrahydrofuran / 0.17 h / -80 °C

8.2: 84.4 percent / tetrahydrofuran / 0.33 h / -80 °C

9.1: 100 percent / H₂; cyclohexane / Lindlar catalyst / CH₂Cl₂ / 1 h / 20 °C

10.1: 83.5 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

11.1: 85 percent / I₂ / diethyl ether / 2 h / 20 °C

12.1: Cs₂CO₃ / acetone / 7 h / 15 °C

With pyridine; hydrogenchloride; disodium hydrogenphosphate; n-butyllithium; tetrapropylammonium perruthennate; sodium amalgam; cyclohexane; 4 A molecular sieve; hydrogen; iodine; caesium carbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; isopropyl alcohol; acetone; 12.1: intramolecular Michael reaction;

DOI:10.1021/jo035193y

upstream raw materials:

(6S,13S,2E,9E)-15-benzenesulfinyl-13-isopropyl-6,10-dimethyl-4,14-dioxo-pentadeca-2,9-dienoic acid methyl ester

(S)-3,7-dimethyl-6-octen-1-ol

2,2-dimethyl-propionic acid (3S)-3,7-dimethyl-oct-6-enyl ester

(S)-3-methyl-2-((phenylsulfonyl)methyl)butan-1-ol