Pentanoic acid, 5-[6-(dimethylphenylsilyl)octahydro-1-(4-methyl-3-oxo-1-nonen-6-ynyl)-2 -[(tetrahydro-2H-pyran-2-yl)oxy]-5H-inden-5-ylidene]-, methyl ester

Base Information

• Chemical Name: Pentanoic acid, 5-[6-(dimethylphenylsilyl)octahydro-1-(4-methyl-3-oxo-1-nonen-6-ynyl)-2 -[(tetrahydro-2H-pyran-2-yl)oxy]-5H-inden-5-ylidene]-, methyl ester
• CAS No.: 113208-31-4
• Molecular Formula: C₃₈H₅₄O₅Si
• Molecular Weight: 618.929
• Mol file: 113208-31-4.mol

Synonyms:

Chemical Property of Pentanoic acid, 5-[6-(dimethylphenylsilyl)octahydro-1-(4-methyl-3-oxo-1-nonen-6-ynyl)-2 -[(tetrahydro-2H-pyran-2-yl)oxy]-5H-inden-5-ylidene]-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Pentanoic acid, 5-[6-(dimethylphenylsilyl)octahydro-1-(4-methyl-3-oxo-1-nonen-6-ynyl)-2 -[(tetrahydro-2H-pyran-2-yl)oxy]-5H-inden-5-ylidene]-, methyl ester

There total 12 articles about Pentanoic acid, 5-[6-(dimethylphenylsilyl)octahydro-1-(4-methyl-3-oxo-1-nonen-6-ynyl)-2 -[(tetrahydro-2H-pyran-2-yl)oxy]-5H-inden-5-ylidene]-, methyl ester 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:

(E)-4-[(1R,2S,3R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-but-2-enoic acid methyl ester (113208-22-3,118628-90-3) → 5-[(1R,2R,3aS,7aS)-6-(Dimethyl-phenyl-silanyl)-1-((E)-4-methyl-3-oxo-non-1-en-6-ynyl)-2-(tetrahydro-pyran-2-yloxy)-octahydro-inden-(5E)-ylidene]-pentanoic acid methyl ester (113208-31-4,113428-26-5,113428-29-8,113428-30-1,113428-31-2)

Guidance literature:

Multi-step reaction with 11 steps

1: Zn, TiCl₄ / Ambient temperature

2: 1.)Siam₂BH, 2.) 30percent H₂O₂, 6N NaOH / 1.) THF, 0 deg C, 2.) THF, 0 deg C

3: 98 percent / LiAlH₄ / tetrahydrofuran / 0 °C

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C

5: dibenzylammonium trifluoroacetate / toluene / 110 °C

6: 1.) t-BuOK / THF, RT

7: diethyl ether / 0 °C

8: 60 percent / H₂ / 10percent Pd-C / methanol / 25 °C / 760 Torr

9: 81 percent / TBAF / tetrahydrofuran / 2.5 h / Ambient temperature

10: SO₃*Py, Et₃N, DMSO / Ambient temperature

11: NaH / tetrahydrofuran / Ambient temperature

With sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; pyridine-SO₃ complex; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; titanium tetrachloride; sodium hydride; dimethyl sulfoxide; triethylamine; zinc; dibenzylammonium trifluoroacetate salt; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; toluene;

DOI:10.1016/S0040-4039(00)96003-9

Reference yield:

(2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-[2-(dimethyl-phenyl-silanyl)-4-oxo-butyl]-4-(tetrahydro-pyran-2-yloxy)-cyclopentanecarbaldehyde (113331-54-7,113428-24-3) → 5-[(1R,2R,3aS,7aS)-6-(Dimethyl-phenyl-silanyl)-1-((E)-4-methyl-3-oxo-non-1-en-6-ynyl)-2-(tetrahydro-pyran-2-yloxy)-octahydro-inden-(5E)-ylidene]-pentanoic acid methyl ester (113208-31-4,113428-26-5,113428-29-8,113428-30-1,113428-31-2)

Guidance literature:

Multi-step reaction with 7 steps

1: dibenzylammonium trifluoroacetate / toluene / 110 °C

2: 1.) t-BuOK / THF, RT

3: diethyl ether / 0 °C

4: 60 percent / H₂ / 10percent Pd-C / methanol / 25 °C / 760 Torr

5: 81 percent / TBAF / tetrahydrofuran / 2.5 h / Ambient temperature

6: SO₃*Py, Et₃N, DMSO / Ambient temperature

7: NaH / tetrahydrofuran / Ambient temperature

With pyridine-SO₃ complex; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; dibenzylammonium trifluoroacetate salt; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; toluene;

DOI:10.1016/S0040-4039(00)96003-9

Reference yield:

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one (65025-95-8) → 5-[(1R,2R,3aS,7aS)-6-(Dimethyl-phenyl-silanyl)-1-((E)-4-methyl-3-oxo-non-1-en-6-ynyl)-2-(tetrahydro-pyran-2-yloxy)-octahydro-inden-(5E)-ylidene]-pentanoic acid methyl ester (113208-31-4,113428-26-5,113428-29-8,113428-30-1,113428-31-2)

Guidance literature:

Multi-step reaction with 14 steps

1: DIBAH / toluene / -78 °C

2: toluene / 60 °C

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C

4: Zn, TiCl₄ / Ambient temperature

5: 1.)Siam₂BH, 2.) 30percent H₂O₂, 6N NaOH / 1.) THF, 0 deg C, 2.) THF, 0 deg C

6: 98 percent / LiAlH₄ / tetrahydrofuran / 0 °C

7: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C

8: dibenzylammonium trifluoroacetate / toluene / 110 °C

9: 1.) t-BuOK / THF, RT

10: diethyl ether / 0 °C

11: 60 percent / H₂ / 10percent Pd-C / methanol / 25 °C / 760 Torr

12: 81 percent / TBAF / tetrahydrofuran / 2.5 h / Ambient temperature

13: SO₃*Py, Et₃N, DMSO / Ambient temperature

14: NaH / tetrahydrofuran / Ambient temperature

With sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; pyridine-SO₃ complex; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; zinc; dibenzylammonium trifluoroacetate salt; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; toluene;

DOI:10.1016/S0040-4039(00)96003-9

upstream raw materials:

3-methyl-2-oxo-oct-5-ynyl-phosphonic acid-dimethylester

5-[(1R,2R,3aS,7aS)-6-(Dimethyl-phenyl-silanyl)-1-formyl-2-(tetrahydro-pyran-2-yloxy)-octahydro-inden-(5E)-ylidene]-pentanoic acid methyl ester

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

(E)-4-[(1R,2S,3R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-but-2-enoic acid methyl ester

Downstream raw materials:

5-[(1R,2R,3aS,7aS)-6-(Dimethyl-phenyl-silanyl)-1-((E)-(R)-3-hydroxy-4-methyl-non-1-en-6-ynyl)-2-(tetrahydro-pyran-2-yloxy)-octahydro-inden-(5E)-ylidene]-pentanoic acid methyl ester

5-[(1R,2R,3aS,7aS)-6-(Dimethyl-phenyl-silanyl)-1-((E)-(S)-3-hydroxy-4-methyl-non-1-en-6-ynyl)-2-(tetrahydro-pyran-2-yloxy)-octahydro-inden-(5E)-ylidene]-pentanoic acid methyl ester

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