(+)-(3'S,4'S)-seselin epoxide

Base Information

• Chemical Name: (+)-(3'S,4'S)-seselin epoxide
• CAS No.: 1148112-58-6
• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.247
• Mol file: 1148112-58-6.mol

Synonyms:(+)-(3'S,4'S)-seselin epoxide

Chemical Property of (+)-(3'S,4'S)-seselin epoxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(3'S,4'S)-seselin epoxide

There total 2 articles about (+)-(3'S,4'S)-seselin epoxide 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%

seseline (523-59-1) → (+)-(3'S,4'S)-seselin epoxide (1148112-58-6)

Guidance literature:

With tetraphenylphosphonium monoperoxysulfate; (+)-N-{(4S,5S)-2,2-dimethyl-4-[4-(methylsulfonyl)phenyl]-1,3-dioxan-5-yl}-3,4-dihydroisoquinolinium tetraphenylborate; In dichloromethane; at -20 ℃; for 24h; Reagent/catalyst; enantioselective reaction;

DOI:10.1039/c3cy00352c

Reference yield:

seseline (523-59-1) → (+)-(3'S,4'S)-seselin epoxide (1148112-58-6) + (-)-(3'R,4'R)-seselin epoxide

Guidance literature:

With potassium peroxymonosulfate; sodium carbonate; (-)-N-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]-5H-dibenzo[c,e]azepinium tetraphenylborate; In water; acetonitrile; at 0 ℃; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/jo300915u

Reference yield: 95.0%

(+)-(3'S,4'S)-seselin epoxide (1148112-58-6) → (+)-(3'S,4'R)-trans-khellactone (518-76-3,4968-31-4,15575-68-5,15645-11-1,23458-04-0,24144-61-4,54712-23-1,80124-45-4,20516-17-0)

Guidance literature:

With sulfuric acid; In water; acetone; at 20 ℃; for 1h; optical yield given as %ee;

DOI:10.1021/ol900444h

upstream raw materials:

seseline

Downstream raw materials:

(+)-(3'S,4'R)-trans-khellactone

Refernces

• 1、 Page, Philip C. Bulman,Appleby, Louise F.,Day, David,Chan, Yohan,Buckley, Benjamin R.,Allin, Steven M.,McKenzie, Michael J.. "Highly enantioselective total synthesis of (-)-(3'S)-lomatin and (+)-(3'S,4'/?)-frans-khellactone". . p. 1991 - 1993. Retrieved 2009.