ethyl (+)-(2E,4S)-4-(tert-butyldimethylsilyloxy)-5-(p-tolylsulfonyl)-2-pentenoate

Base Information

Chemical Name:ethyl (+)-(2E,4S)-4-(tert-butyldimethylsilyloxy)-5-(p-tolylsulfonyl)-2-pentenoate
CAS No.:781671-97-4
Molecular Formula:C₂₀H₃₂O₅SSi
Molecular Weight:412.623
Hs Code.:

Synonyms:ethyl (+)-(2E,4S)-4-(tert-butyldimethylsilyloxy)-5-(p-tolylsulfonyl)-2-pentenoate

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Chemical Property of ethyl (+)-(2E,4S)-4-(tert-butyldimethylsilyloxy)-5-(p-tolylsulfonyl)-2-pentenoate

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Technology Process of ethyl (+)-(2E,4S)-4-(tert-butyldimethylsilyloxy)-5-(p-tolylsulfonyl)-2-pentenoate

There total 11 articles about ethyl (+)-(2E,4S)-4-(tert-butyldimethylsilyloxy)-5-(p-tolylsulfonyl)-2-pentenoate 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%

: 781671-93-0
ethyl (+)-[2E,4S,(S)R]-4-(tert-butyldimethylsilyloxy)-5-(p-tolylsulfinyl)pent-2-enoate

: 781671-97-4
ethyl (+)-(2E,4S)-4-(tert-butyldimethylsilyloxy)-5-(p-tolylsulfonyl)-2-pentenoate

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1021/ol048577z

Reference yield:

: 1519-39-7
(R)-methyl p-tolyl sulfoxide

: 781671-97-4
ethyl (+)-(2E,4S)-4-(tert-butyldimethylsilyloxy)-5-(p-tolylsulfonyl)-2-pentenoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / 0 °C

1.2: 96 percent / tetrahydrofuran; hexane / 2 h / 0 - 20 °C

2.1: DIBALH; Yb(OTf)3 / tetrahydrofuran / 6 h / -78 °C

3.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 20 °C

4.1: 73 percent / DDQ / CH₂Cl₂ / 8 h / 20 °C

5.1: DCC; pyridine; CF₃COOH / dimethylsulfoxide; benzene / 2 h / 20 °C

6.1: LiCl; DBU / acetonitrile / 2 h / 20 °C

7.1: 100 percent / MCPBA / CH₂Cl₂ / 2 h / 0 °C

With pyridine; 2,6-dimethylpyridine; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; ytterbium(III) triflate; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; benzene; 6.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol048577z

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 781671-97-4
ethyl (+)-(2E,4S)-4-(tert-butyldimethylsilyloxy)-5-(p-tolylsulfonyl)-2-pentenoate

Guidance literature:: Multi-step reaction with 5 steps

1: 2,6-lutidine / CH₂Cl₂ / 20 °C

2: 73 percent / DDQ / CH₂Cl₂ / 8 h / 20 °C

3: DCC; pyridine; CF₃COOH / dimethylsulfoxide; benzene / 2 h / 20 °C

4: LiCl; DBU / acetonitrile / 2 h / 20 °C

5: 100 percent / MCPBA / CH₂Cl₂ / 2 h / 0 °C

With pyridine; 2,6-dimethylpyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In dichloromethane; dimethyl sulfoxide; acetonitrile; benzene; 4: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol048577z