Ethyl (4S,5S,6S)-4,5-epoxy-6-hydroxy-8-<(p-toluenesulfonyl)oxy>-(E)-2-octenoate

Base Information

Chemical Name:Ethyl (4S,5S,6S)-4,5-epoxy-6-hydroxy-8-<(p-toluenesulfonyl)oxy>-(E)-2-octenoate
CAS No.:151953-13-8
Molecular Formula:C₁₇H₂₂O₇S
Molecular Weight:370.423
Hs Code.:

Synonyms:Ethyl (4S,5S,6S)-4,5-epoxy-6-hydroxy-8-<(p-toluenesulfonyl)oxy>-(E)-2-octenoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Ethyl (4S,5S,6S)-4,5-epoxy-6-hydroxy-8-<(p-toluenesulfonyl)oxy>-(E)-2-octenoate

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Technology Process of Ethyl (4S,5S,6S)-4,5-epoxy-6-hydroxy-8-<(p-toluenesulfonyl)oxy>-(E)-2-octenoate

There total 3 articles about Ethyl (4S,5S,6S)-4,5-epoxy-6-hydroxy-8-<(p-toluenesulfonyl)oxy>-(E)-2-octenoate 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: 90.0%

: 151953-12-7
Ethyl (6S)-6-hydroxy-8-<(p-toluenesulfonyl)oxy>-(E,E)-2,4-octadienoate

: 151953-13-8
Ethyl (4S,5S,6S)-4,5-epoxy-6-hydroxy-8-<(p-toluenesulfonyl)oxy>-(E)-2-octenoate

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; In 2,2,4-trimethylpentane; dichloromethane; at -23 ℃;
DOI:10.1021/jo00077a034

Reference yield:

: (4S)-4-(Triisopropyloxy)-6-<(p-toluenesulfonyl)oxy>-(E)-2-hexenal

: 151953-13-8
Ethyl (4S,5S,6S)-4,5-epoxy-6-hydroxy-8-<(p-toluenesulfonyl)oxy>-(E)-2-octenoate

Guidance literature:: Multi-step reaction with 3 steps

1: 89 percent / benzene / 1.5 h / 55 °C

2: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

3: 90 percent / t-BuOOH, Ti(Oi-Pr)4, (+)-DIPT, molecular sieves 4 Angstroem / CH₂Cl₂; 2,2,4-trimethyl-pentane / -23 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; benzene;
DOI:10.1021/jo00077a034

Reference yield:

: 151953-11-6
Ethyl (6S)-6-(triisopropylsiloxy)-8-<(p-toluenesulfonyl)oxy>-(E,E)-2,4-octadienoate

: 151953-13-8
Ethyl (4S,5S,6S)-4,5-epoxy-6-hydroxy-8-<(p-toluenesulfonyl)oxy>-(E)-2-octenoate

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

2: 90 percent / t-BuOOH, Ti(Oi-Pr)4, (+)-DIPT, molecular sieves 4 Angstroem / CH₂Cl₂; 2,2,4-trimethyl-pentane / -23 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane;
DOI:10.1021/jo00077a034