(2S,7R)-7-[(1R,3E)-1-Chloro-5-hexyn-3-enyl]-2-[(R)-1-bromopropyl]-1-oxacyclohepta-4-ene

Base Information

• Chemical Name: (2S,7R)-7-[(1R,3E)-1-Chloro-5-hexyn-3-enyl]-2-[(R)-1-bromopropyl]-1-oxacyclohepta-4-ene
• CAS No.: 81053-29-4
• Molecular Formula: C₁₅H₂₀BrClO
• Molecular Weight: 331.68
• Mol file: 81053-29-4.mol

Synonyms:isolaurepinnacin;(2S,7R)-2-((S)-1-Bromo-propyl)-7-((E)-(R)-1-chloro-hex-3-en-5-ynyl)-2,3,6,7-tetrahydro-oxepine;

Chemical Property of (2S,7R)-7-[(1R,3E)-1-Chloro-5-hexyn-3-enyl]-2-[(R)-1-bromopropyl]-1-oxacyclohepta-4-ene

Chemical Property:

• PSA: 9.23000
• LogP: 4.45060

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,7R)-7-[(1R,3E)-1-Chloro-5-hexyn-3-enyl]-2-[(R)-1-bromopropyl]-1-oxacyclohepta-4-ene

There total 27 articles about (2S,7R)-7-[(1R,3E)-1-Chloro-5-hexyn-3-enyl]-2-[(R)-1-bromopropyl]-1-oxacyclohepta-4-ene 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:

(+/-)-1,1-dimethoxy-5-(triisopropylsiloxy)pent-3-yn-2-ol (151074-01-0) → (+)-isolaurepinnacin (81053-29-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 88 percent / Jones reagent / acetone / 0 °C

2.1: (R)-(-)-BINAL-H / tetrahydrofuran / 17 h / -100 - -85 °C

3.1: 97 percent / H₂ / Pd/BaSO₄ / methanol / 3 h / 20 °C / 760 Torr

4.1: pyridine / CH₂Cl₂ / 1 h / 0 °C

5.1: 445 mg / (n-Bu)4NCl / CH₂Cl₂ / 12 h / 0 - 23 °C

6.1: Me₂BBr / CH₂Cl₂ / 2.1 h / -78 - 23 °C

7.1: 203 mg / i-Pr₂NEt; AgOTf / CH₂Cl₂ / 3 h / 0 - 23 °C

8.1: BCl₃ / CH₂Cl₂ / 0.17 h / -78 °C

9.1: BCl₃ / CH₂Cl₂ / 0.58 h / -78 - 23 °C

10.1: 30 mg / TBAF / tetrahydrofuran / 4 h / 0 - 23 °C

11.1: Dess-Martin periodinane / CH₂Cl₂ / 0.42 h / 23 °C

12.1: 31 mg / tetrahydrofuran / 1 h / -78 - 23 °C

13.1: Co₂(CO)8 / diethyl ether / 2 h / -23 - 0 °C

13.2: Tf₂O / CH₂Cl₂ / 2 h / -78 - -5 °C

13.3: (NH₄)2Ce(NO₃)6 / acetone / 23 °C

With pyridine; jones reagent; dicobalt octacarbonyl; dimethylboron bromide; (R)-(-)-BINAL-H; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; hydrogen; silver trifluoromethanesulfonate; boron trichloride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; 1.1: Jones oxidation / 2.1: Reduction / 3.1: Hydrogenation / 4.1: Esterification / 5.1: Substitution / 6.1: Bromination / 7.1: Substitution / 8.1: Substitution / 9.1: Prins cyclization / 10.1: desilylation / 11.1: Dess-Martin oxidation / 12.1: Addition / 13.1: complexation / 13.2: Dehydration / 13.3: decomplexation;

DOI:10.1021/ja964080b

Reference yield:

1,1-dimethoxy-5-(triisopropylsiloxy)pent-3-yn-2-one (187743-78-8) → (+)-isolaurepinnacin (81053-29-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: (R)-(-)-BINAL-H / tetrahydrofuran / 17 h / -100 - -85 °C

2.1: 97 percent / H₂ / Pd/BaSO₄ / methanol / 3 h / 20 °C / 760 Torr

3.1: pyridine / CH₂Cl₂ / 1 h / 0 °C

4.1: 445 mg / (n-Bu)4NCl / CH₂Cl₂ / 12 h / 0 - 23 °C

5.1: Me₂BBr / CH₂Cl₂ / 2.1 h / -78 - 23 °C

6.1: 203 mg / i-Pr₂NEt; AgOTf / CH₂Cl₂ / 3 h / 0 - 23 °C

7.1: BCl₃ / CH₂Cl₂ / 0.17 h / -78 °C

8.1: BCl₃ / CH₂Cl₂ / 0.58 h / -78 - 23 °C

9.1: 30 mg / TBAF / tetrahydrofuran / 4 h / 0 - 23 °C

10.1: Dess-Martin periodinane / CH₂Cl₂ / 0.42 h / 23 °C

11.1: 31 mg / tetrahydrofuran / 1 h / -78 - 23 °C

12.1: Co₂(CO)8 / diethyl ether / 2 h / -23 - 0 °C

12.2: Tf₂O / CH₂Cl₂ / 2 h / -78 - -5 °C

12.3: (NH₄)2Ce(NO₃)6 / acetone / 23 °C

With pyridine; dicobalt octacarbonyl; dimethylboron bromide; (R)-(-)-BINAL-H; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; hydrogen; silver trifluoromethanesulfonate; boron trichloride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1.1: Reduction / 2.1: Hydrogenation / 3.1: Esterification / 4.1: Substitution / 5.1: Bromination / 6.1: Substitution / 7.1: Substitution / 8.1: Prins cyclization / 9.1: desilylation / 10.1: Dess-Martin oxidation / 11.1: Addition / 12.1: complexation / 12.2: Dehydration / 12.3: decomplexation;

DOI:10.1021/ja964080b

Reference yield:

(2S)-1,1-dimethoxy-5-(triisopropylsiloxy)pent-3-yn-2-ol (151074-09-8) → (+)-isolaurepinnacin (81053-29-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 97 percent / H₂ / Pd/BaSO₄ / methanol / 3 h / 20 °C / 760 Torr

2.1: pyridine / CH₂Cl₂ / 1 h / 0 °C

3.1: 445 mg / (n-Bu)4NCl / CH₂Cl₂ / 12 h / 0 - 23 °C

4.1: Me₂BBr / CH₂Cl₂ / 2.1 h / -78 - 23 °C

5.1: 203 mg / i-Pr₂NEt; AgOTf / CH₂Cl₂ / 3 h / 0 - 23 °C

6.1: BCl₃ / CH₂Cl₂ / 0.17 h / -78 °C

7.1: BCl₃ / CH₂Cl₂ / 0.58 h / -78 - 23 °C

8.1: 30 mg / TBAF / tetrahydrofuran / 4 h / 0 - 23 °C

9.1: Dess-Martin periodinane / CH₂Cl₂ / 0.42 h / 23 °C

10.1: 31 mg / tetrahydrofuran / 1 h / -78 - 23 °C

11.1: Co₂(CO)8 / diethyl ether / 2 h / -23 - 0 °C

11.2: Tf₂O / CH₂Cl₂ / 2 h / -78 - -5 °C

11.3: (NH₄)2Ce(NO₃)6 / acetone / 23 °C

With pyridine; dicobalt octacarbonyl; dimethylboron bromide; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; hydrogen; silver trifluoromethanesulfonate; boron trichloride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1.1: Hydrogenation / 2.1: Esterification / 3.1: Substitution / 4.1: Bromination / 5.1: Substitution / 6.1: Substitution / 7.1: Prins cyclization / 8.1: desilylation / 9.1: Dess-Martin oxidation / 10.1: Addition / 11.1: complexation / 11.2: Dehydration / 11.3: decomplexation;

DOI:10.1021/ja964080b

upstream raw materials:

(2S,7R)-2-[(1S)-1-bromopropyl]-7-[(1R)-chloro-(4RS)-hydroxy-5-hexynyl]-2,3,6,7-tetrahydrooxepin

[(2S,3R)-3-ethyloxiran-2-yl]methanol

(2S,3S)-3-bromo-1,2-epoxypentane

(5S,6S)-6-Bromo-5-hydroxy-2-(trimethylsilyl)-1-octene

Refernces

• 1、 Berger,Overman,Renhowe. "Enantioselective total synthesis of (+)-isolaurepunnacin". . p. 9305 - 9306. Retrieved 2007/10/02.