(4S)-4-hydroxy-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-ynyl acetate

Base Information

Chemical Name:(4S)-4-hydroxy-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-ynyl acetate
CAS No.:847049-74-5
Molecular Formula:C₂₆H₃₆O₅
Molecular Weight:428.569
Hs Code.:

Synonyms:(4S)-4-hydroxy-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-ynyl acetate

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Chemical Property of (4S)-4-hydroxy-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-ynyl acetate

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Technology Process of (4S)-4-hydroxy-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-ynyl acetate

There total 11 articles about (4S)-4-hydroxy-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-ynyl acetate 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%

: 627-09-8
Propargyl acetate

: 847049-73-4
(1R,2S)-2-{(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl}cyclopentanecarbaldehyde

: 847049-74-5
(4S)-4-hydroxy-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-ynyl acetate

: Acetic acid (R)-4-hydroxy-4-{(1R,2S)-2-[(E)-(S)-6-(4-methoxy-benzyloxy)-hept-1-enyl]-cyclopentyl}-but-2-ynyl ester

Guidance literature:: With (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine; In toluene; at 23 ℃; optical yield given as %de; Inert atmosphere;
DOI:10.1002/ejoc.200901233

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 847049-74-5
(4S)-4-hydroxy-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-ynyl acetate

Guidance literature:: Multi-step reaction with 6 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

With lithium aluminium tetrahydride; oxalyl dichloride; zinc trifluoromethanesulfonate; sodium hydride; caesium carbonate; (+)-N-methylephedrine; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; [1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) chloride-dichlormethane complex; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 5.1: Swern oxidation;
DOI:10.1055/s-2004-835669

Reference yield:

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

: 847049-74-5
(4S)-4-hydroxy-4-{(1R,2S)-2-[(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl]cyclopentyl}but-2-ynyl acetate

Guidance literature:: Multi-step reaction with 8 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

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