(Z)-3-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}propyl octanoate

Base Information

• Chemical Name: (Z)-3-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}propyl octanoate
• CAS No.: 663601-35-2
• Molecular Formula: C₃₂H₅₀O₅
• Molecular Weight: 514.746
• Mol file: 663601-35-2.mol

Synonyms:(Z)-3-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}propyl octanoate

Chemical Property of (Z)-3-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}propyl octanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-3-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}propyl octanoate

There total 21 articles about (Z)-3-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}propyl octanoate 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: 91.0%

n-octanoic acid chloride (111-64-8) + (Z)-5-(3-hydroxypropyl)-3-[4-methyl-3-(methylethyl)pentylidene]-5-[(phenylmethoxy)methyl]-4,5-dihydrofuran-2-one (663601-33-0) → (Z)-3-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}propyl octanoate (663601-35-2)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃;

DOI:10.1021/jm030454h

Reference yield:

(2S)-3-(benzyloxy)propane-1,2-diol (17325-85-8) → (Z)-3-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}propyl octanoate (663601-35-2)

Guidance literature:

Multi-step reaction with 21 steps

1.1: imidazole / CH₂Cl₂ / 1.42 h / 20 °C

1.2: CH₂Cl₂; dimethylformamide / 20 °C

2.1: 46.9 g / pyridinium chlorochromate; 4A molecular sieves / CH₂Cl₂ / 2 h / Heating

3.1: tetrahydrofuran / 0 - 20 °C

4.1: BH₃*SMe₂ / tetrahydrofuran / -78 - 20 °C

4.2: 31.7 g / pyridinium chlorochromate; 4A molecular sieves / CH₂Cl₂ / 48 h

5.1: diisobutylaluminum hydride / tetrahydrofuran; toluene / -78 °C

6.1: Dowex 50WX₈-200; aq. AcOH / tetrahydrofuran

7.1: TBAF / tetrahydrofuran / 0 - 20 °C

8.1: 1,3-dicyclohexylcarbodiimide; dichloroacetic acid; DMSO / 16 h

9.1: t-BuOK / tetrahydrofuran / 0.5 h

9.2: 240 mg / tetrahydrofuran

10.1: BH₃*SMe₂ / tetrahydrofuran / 17 h / -78 - 0 °C

10.2: 56 percent / NaBO₃*H₂O / tetrahydrofuran / 2 h / 0 - 20 °C

11.1: 1,3-dicyclohexylcarbodiimide; dichloroacetic acid; DMSO / 16 h

12.1: t-BuOK / tetrahydrofuran / 0.5 h

12.2: 150 mg / tetrahydrofuran

13.1: BH₃*SMe₂ / tetrahydrofuran / 17 h / -78 - 0 °C

13.2: 66 percent / NaBO₃*H₂O / tetrahydrofuran / 2 h / 0 - 20 °C

14.1: NaH / tetrahydrofuran / 0 °C

14.2: 80 percent / Bu₄NI / tetrahydrofuran / Heating

15.1: 46 percent / aq. HCl / tetrahydrofuran / 0 - 20 °C

16.1: 89 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; 4A molecular sieves / CH₂Cl₂; acetonitrile / 0 - 20 °C

17.1: LDA / tetrahydrofuran; heptane; ethylbenzene / 2 h / -78 °C

17.2: tetrahydrofuran; heptane; ethylbenzene / -78 °C

18.1: Et₃N / CH₂Cl₂ / 2.5 h / 0 - 20 °C

19.1: 58 mg / DBU / CH₂Cl₂ / 3 h / 20 °C

20.1: 58 percent / aq. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 2.5 h

21.1: 91 percent / pyridine / CH₂Cl₂ / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; dichloro-acetic acid; tetrapropylammonium perruthennate; dimethylsulfide borane complex; 4 A molecular sieve; DOWEX 50WX₈-200; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; dichloromethane; ethylbenzene; toluene; acetonitrile;

DOI:10.1021/jm030454h

Reference yield:

3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-1-(phenylmethoxy)aceton (335393-68-5) → (Z)-3-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}propyl octanoate (663601-35-2)

Guidance literature:

Multi-step reaction with 19 steps

1.1: tetrahydrofuran / 0 - 20 °C

2.1: BH₃*SMe₂ / tetrahydrofuran / -78 - 20 °C

2.2: 31.7 g / pyridinium chlorochromate; 4A molecular sieves / CH₂Cl₂ / 48 h

3.1: diisobutylaluminum hydride / tetrahydrofuran; toluene / -78 °C

4.1: Dowex 50WX₈-200; aq. AcOH / tetrahydrofuran

5.1: TBAF / tetrahydrofuran / 0 - 20 °C

6.1: 1,3-dicyclohexylcarbodiimide; dichloroacetic acid; DMSO / 16 h

7.1: t-BuOK / tetrahydrofuran / 0.5 h

7.2: 240 mg / tetrahydrofuran

8.1: BH₃*SMe₂ / tetrahydrofuran / 17 h / -78 - 0 °C

8.2: 56 percent / NaBO₃*H₂O / tetrahydrofuran / 2 h / 0 - 20 °C

9.1: 1,3-dicyclohexylcarbodiimide; dichloroacetic acid; DMSO / 16 h

10.1: t-BuOK / tetrahydrofuran / 0.5 h

10.2: 150 mg / tetrahydrofuran

11.1: BH₃*SMe₂ / tetrahydrofuran / 17 h / -78 - 0 °C

11.2: 66 percent / NaBO₃*H₂O / tetrahydrofuran / 2 h / 0 - 20 °C

12.1: NaH / tetrahydrofuran / 0 °C

12.2: 80 percent / Bu₄NI / tetrahydrofuran / Heating

13.1: 46 percent / aq. HCl / tetrahydrofuran / 0 - 20 °C

14.1: 89 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; 4A molecular sieves / CH₂Cl₂; acetonitrile / 0 - 20 °C

15.1: LDA / tetrahydrofuran; heptane; ethylbenzene / 2 h / -78 °C

15.2: tetrahydrofuran; heptane; ethylbenzene / -78 °C

16.1: Et₃N / CH₂Cl₂ / 2.5 h / 0 - 20 °C

17.1: 58 mg / DBU / CH₂Cl₂ / 3 h / 20 °C

18.1: 58 percent / aq. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 2.5 h

19.1: 91 percent / pyridine / CH₂Cl₂ / 0 °C

With pyridine; hydrogenchloride; dichloro-acetic acid; tetrapropylammonium perruthennate; dimethylsulfide borane complex; 4 A molecular sieve; DOWEX 50WX₈-200; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; dichloromethane; ethylbenzene; toluene; acetonitrile;

DOI:10.1021/jm030454h

upstream raw materials:

n-octanoic acid chloride

(Z)-5-(3-hydroxypropyl)-3-[4-methyl-3-(methylethyl)pentylidene]-5-[(phenylmethoxy)methyl]-4,5-dihydrofuran-2-one

(2S)-3-(benzyloxy)propane-1,2-diol

3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-1-(phenylmethoxy)aceton