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

Base Information

Chemical Name:ethyl (+)-[2E,4S,(S)R]-4-(tert-butyldimethylsilyloxy)-5-(p-tolylsulfinyl)pent-2-enoate
CAS No.:781671-93-0
Molecular Formula:C₂₀H₃₂O₄SSi
Molecular Weight:396.623
Hs Code.:

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

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Chemical Property of ethyl (+)-[2E,4S,(S)R]-4-(tert-butyldimethylsilyloxy)-5-(p-tolylsulfinyl)pent-2-enoate

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Technology Process of ethyl (+)-[2E,4S,(S)R]-4-(tert-butyldimethylsilyloxy)-5-(p-tolylsulfinyl)pent-2-enoate

There total 9 articles about ethyl (+)-[2E,4S,(S)R]-4-(tert-butyldimethylsilyloxy)-5-(p-tolylsulfinyl)pent-2-enoate 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:

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 781671-92-9
(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-toluene-4-sulfinyl)-propionaldehyde

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

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In acetonitrile; at 20 ℃; for 2h;
DOI:10.1021/ol048577z

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

With pyridine; 2,6-dimethylpyridine; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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

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

Guidance literature:: Multi-step reaction with 4 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

With pyridine; 2,6-dimethylpyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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