(2E,4R)-4-[(tert-butyldiphenylsilyl)oxy]-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-enoic acid

Base Information

Chemical Name:(2E,4R)-4-[(tert-butyldiphenylsilyl)oxy]-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-enoic acid
CAS No.:847049-78-9
Molecular Formula:C₄₀H₅₂O₅Si
Molecular Weight:640.935
Hs Code.:

Synonyms:(2E,4R)-4-[(tert-butyldiphenylsilyl)oxy]-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-enoic acid

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Chemical Property of (2E,4R)-4-[(tert-butyldiphenylsilyl)oxy]-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-enoic acid

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Technology Process of (2E,4R)-4-[(tert-butyldiphenylsilyl)oxy]-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-enoic acid

There total 13 articles about (2E,4R)-4-[(tert-butyldiphenylsilyl)oxy]-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-enoic acid 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: 98.0%

: 847049-77-8
(2E,4R)-4-[(tert-butyldiphenylsilyl)oxy]-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-enal

: 847049-78-9
(2E,4R)-4-[(tert-butyldiphenylsilyl)oxy]-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-enoic acid

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol; at 20 ℃; for 24h;
DOI:10.1055/s-2004-835669

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 847049-78-9
(2E,4R)-4-[(tert-butyldiphenylsilyl)oxy]-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-enoic acid

Guidance literature:: Multi-step reaction with 9 steps

1.1: NaH / dimethylformamide; tetrahydrofuran / 15 h / 0 - 20 °C

2.1: tetrahydrofuran / 3 h / 30 °C

3.1: aq. Cs₂CO₃ / [Pd(dppf)Cl₂*CH₂Cl₂] / dimethylformamide; tetrahydrofuran / 6 h / 30 °C

4.1: 85 percent / LiAlH₄ / diethyl ether / 3 h / 0 - 25 °C

5.1: 89 percent / (COCl)2; DMSO; DIEA / CH₂Cl₂ / -60 - 20 °C

6.1: Zn(OTf)2; (+)-N-methylephedrine; Et₃N / toluene / 0.25 h / 23 °C

6.2: toluene / 24 h / 23 °C

7.1: 96 percent / imidazole / dimethylformamide / 12 h / 0 - 20 °C

8.1: PPh₃ / Pd(PPh₃)4 / toluene / 0.33 h / 20 °C

8.2: 33 percent / toluene / 1 h / 110 °C

9.1: 98 percent / 2-methyl-2-butene; NaO₂Cl; aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 24 h / 20 °C

With 1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 2-methyl-but-2-ene; oxalyl dichloride; zinc trifluoromethanesulfonate; sodium hydride; caesium carbonate; (+)-N-methylephedrine; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; [1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) chloride-dichlormethane complex; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 5.1: Swern oxidation;
DOI:10.1055/s-2004-835669

Reference yield:

: cis-2-carbomethoxy cyclopentane-1-carboxylic acid

: 847049-78-9
(2E,4R)-4-[(tert-butyldiphenylsilyl)oxy]-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-enoic acid

Guidance literature:: Multi-step reaction with 11 steps

1.1: 92 percent / t-BuOK / tetrahydrofuran / 1 h / 0 - 20 °C

2.1: 60 percent / BH₃*SMe₂ / tetrahydrofuran / 12 h / -20 - 20 °C

3.1: 96 percent / (COCl)2; DMSO; DIEA / CH₂Cl₂ / -60 - 20 °C

4.1: 75 percent / CrCl₂ / tetrahydrofuran; dioxane / 72 h / 25 °C

5.1: aq. Cs₂CO₃ / [Pd(dppf)Cl₂*CH₂Cl₂] / dimethylformamide; tetrahydrofuran / 6 h / 30 °C

6.1: 85 percent / LiAlH₄ / diethyl ether / 3 h / 0 - 25 °C

7.1: 89 percent / (COCl)2; DMSO; DIEA / CH₂Cl₂ / -60 - 20 °C

8.1: Zn(OTf)2; (+)-N-methylephedrine; Et₃N / toluene / 0.25 h / 23 °C

8.2: toluene / 24 h / 23 °C

9.1: 96 percent / imidazole / dimethylformamide / 12 h / 0 - 20 °C

10.1: PPh₃ / Pd(PPh₃)4 / toluene / 0.33 h / 20 °C

10.2: 33 percent / toluene / 1 h / 110 °C

11.1: 98 percent / 2-methyl-2-butene; NaO₂Cl; aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 24 h / 20 °C

With 1H-imidazole; chromium dichloride; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 2-methyl-but-2-ene; oxalyl dichloride; dimethylsulfide borane complex; potassium tert-butylate; zinc trifluoromethanesulfonate; caesium carbonate; (+)-N-methylephedrine; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; [1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) chloride-dichlormethane complex; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 3.1: Swern oxidation / 7.1: Swern oxidation;
DOI:10.1055/s-2004-835669