(-)-(2S,3S,6E)-2,3-epoxy-2,6-dimethyl-8-(4-methylbenzenesulfonyl)-6-octen-1-ol

Base Information

• Chemical Name: (-)-(2S,3S,6E)-2,3-epoxy-2,6-dimethyl-8-(4-methylbenzenesulfonyl)-6-octen-1-ol
• CAS No.: 142720-38-5
• Molecular Formula: C₁₇H₂₄O₄S
• Molecular Weight: 324.441
• Mol file: 142720-38-5.mol

Synonyms:(-)-(2S,3S,6E)-2,3-epoxy-2,6-dimethyl-8-(4-methylbenzenesulfonyl)-6-octen-1-ol

Chemical Property of (-)-(2S,3S,6E)-2,3-epoxy-2,6-dimethyl-8-(4-methylbenzenesulfonyl)-6-octen-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2S,3S,6E)-2,3-epoxy-2,6-dimethyl-8-(4-methylbenzenesulfonyl)-6-octen-1-ol

There total 10 articles about (-)-(2S,3S,6E)-2,3-epoxy-2,6-dimethyl-8-(4-methylbenzenesulfonyl)-6-octen-1-ol 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: 82.0%

(2E,6E)-3,7-dimethyl-1-(4-methylbenzenesulfonyl)-2,6-octadien-8-ol (70238-35-6) → {(2S,3S)-2-Methyl-3-[(E)-3-methyl-5-(toluene-4-sulfonyl)-pent-3-enyl]-oxiranyl}-methanol (142720-38-5,142793-46-2)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid;

DOI:10.1021/jo00043a014

Reference yield:

(2E,6E)-3,7-dimethyl-1-(4-methylbenzenesulfonyl)-2,6-octadien-8-ol (70238-35-6) → {(2R,3R)-2-Methyl-3-[(E)-3-methyl-5-(toluene-4-sulfonyl)-pent-3-enyl]-oxiranyl}-methanol (142720-38-5,142793-46-2) + (-)-(2S,3S,6E)-2,3-epoxy-2,6-dimethyl-8-(4-methylbenzenesulfonyl)-6-octen-1-ol (142720-38-5)

Guidance literature:

With tert.-butylhydroperoxide; 4 A molecular sieve; titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; In 2,2,4-trimethylpentane; dichloromethane; at -23 ℃; for 3.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00043a014

Reference yield:

(2E,6E)-3,7-dimethyl-1-(4-methylbenzenesulfonyl)-2,6-octadien-8-ol (70238-35-6) → {(2R,3R)-2-Methyl-3-[(E)-3-methyl-5-(toluene-4-sulfonyl)-pent-3-enyl]-oxiranyl}-methanol (142720-38-5,142793-46-2) + (-)-(2S,3S,6E)-2,3-epoxy-2,6-dimethyl-8-(4-methylbenzenesulfonyl)-6-octen-1-ol (142720-38-5)

Guidance literature:

With tert.-butylhydroperoxide; 4 A molecular sieve; titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; In 2,2,4-trimethylpentane; dichloromethane; at -23 ℃; for 3.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00043a014

upstream raw materials:

(2E,6E)-3,7-dimethyl-1-(4-methylbenzenesulfonyl)-2,6-octadien-8-ol

3,7-dimethyl-1-(p-toluenesulfonyl)-2(E),6-octadiene

Downstream raw materials:

(9S/9R,14S,2E,6E,10E)-1-(benzyloxy)-14,15-epoxy-3,11,15-trimethyl-9-(4-methylbenzenesulfonyl)-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatriene

(+)-3β-hydroxy-labda-8(17),13(E)-dien-15-yl benzoate

(+)-3β-hydroxy-(9βH)-labda-8(17),13(E)-dien-15-yl benzoate

(-)-(6S,2E)-6,7-epoxy-3,7-dimethyl-1-(4-methylbenzenesulfonyl)-2-octene