(2S,3S,5Z,8S,9S)-3-Bromo-8-chloro-2-ethyl-2,3,4,7,8,9-hexahydro-9-[(Z)-2-pentene-4-ynyl]oxonin

Base Information

• Chemical Name: (2S,3S,5Z,8S,9S)-3-Bromo-8-chloro-2-ethyl-2,3,4,7,8,9-hexahydro-9-[(Z)-2-pentene-4-ynyl]oxonin
• CAS No.: 71939-43-0
• Molecular Formula: C₁₅H₂₀BrClO
• Molecular Weight: 331.68
• Mol file: 71939-43-0.mol

Synonyms:Oxonin,3-bromo-8-chloro-2-ethyl-2,3,4,7,8,9-hexahydro-9-(2-penten-4-ynyl)-,[2S-[2R*,3R*,5Z,8R*,9R*(Z)]]-; Oxonin,3-bromo-8-chloro-2-ethyl-2,3,4,7,8,9-hexahydro-9-(2Z)-2-penten-4-ynyl-,(2S,3S,5Z,8S,9S)- (9CI); (+)-Obtusenyne; Obtusenyne

Chemical Property of (2S,3S,5Z,8S,9S)-3-Bromo-8-chloro-2-ethyl-2,3,4,7,8,9-hexahydro-9-[(Z)-2-pentene-4-ynyl]oxonin

Chemical Property:

• PSA: 9.23000
• LogP: 4.45060

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5Z,8S,9S)-3-Bromo-8-chloro-2-ethyl-2,3,4,7,8,9-hexahydro-9-[(Z)-2-pentene-4-ynyl]oxonin

There total 105 articles about (2S,3S,5Z,8S,9S)-3-Bromo-8-chloro-2-ethyl-2,3,4,7,8,9-hexahydro-9-[(Z)-2-pentene-4-ynyl]oxonin 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: 100.0%

[(Z)-5-((Z)-(2S,3S,8S,9S)-8-Bromo-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-pent-3-en-1-ynyl]-trimethyl-silane (225642-98-8) → (+)-obtusenyne (71939-43-0)

Guidance literature:

With hydrogen fluoride; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 37 ℃; for 2.5h;

DOI:10.1021/jo990212i

Reference yield: 97.0%

[5-((2S,3S,8S,9S)-8-bromo-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-pent-3-en-1-ynyl]-triethyl-silane (558459-56-6) → (+)-obtusenyne (71939-43-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -78 - 0 ℃;

DOI:10.1021/ja029956v

Reference yield: 70.0%

(Z,2S,3R,8S,9S)-8-bromo-9-ethyl-3-hydroxy-2-((Z)-pent-2-en-4-ynyl)-2,3,4,7,8,9-hexahydrooxonine (558459-57-7) → (+)-obtusenyne (71939-43-0)

Guidance literature:

With tetrachloromethane; 1-methylcyclohex-1-ene; TOP; In toluene;

DOI:10.1021/ja029956v

upstream raw materials:

[(Z)-5-((Z)-(2S,3S,8S,9S)-8-Bromo-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-pent-3-en-1-ynyl]-trimethyl-silane

(Z,2S,3R,8S,9S)-8-bromo-9-ethyl-3-hydroxy-2-((Z)-pent-2-en-4-ynyl)-2,3,4,7,8,9-hexahydrooxonine

[5-((2S,3S,8S,9S)-8-bromo-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-pent-3-en-1-ynyl]-triethyl-silane

4-[1-(4-methoxy-benzyloxy)-pent-4-ynyl]-2,2-dimethyl-[1,3]dioxolane

Refernces

• 1、 Uemura, Toshiyuki,Suzuki, Toshio,Onodera, Naohiro,Hagiwara, Hisahiro,Hoshi, Takashi. "Total synthesis of (+)-obtusenyne". . p. 715 - 719. Retrieved 2007/10/03.
• 2、 Crimmins, Michael T.,Powell, Mark T.. "Enantioselective total synthesis of (+)-obtusenyne". . p. 7592 - 7595. Retrieved 2007/10/03.