(E,3aR^*,5S^*,6aR^*)-3-(phenylmethyl)-2-oxo-3,3a,4,5,6,6a-hexahydro-5-<1-<<(triisopropylsilyl)oxy>methyl>propenyl>-6a-<1-<2-(trimethylacetamido)phenyl>ethenyl>-2H-cyclopentoxazole

Base Information

• Chemical Name: (E,3aR^*,5S^*,6aR^*)-3-(phenylmethyl)-2-oxo-3,3a,4,5,6,6a-hexahydro-5-<1-<<(triisopropylsilyl)oxy>methyl>propenyl>-6a-<1-<2-(trimethylacetamido)phenyl>ethenyl>-2H-cyclopentoxazole
• CAS No.: 97552-32-4
• Molecular Formula: C₃₉H₅₆N₂O₄Si
• Molecular Weight: 644.97

Synonyms:(E,3aR^*,5S^*,6aR^*)-3-(phenylmethyl)-2-oxo-3,3a,4,5,6,6a-hexahydro-5-<1-<<(triisopropylsilyl)oxy>methyl>propenyl>-6a-<1-<2-(trimethylacetamido)phenyl>ethenyl>-2H-cyclopentoxazole

Chemical Property of (E,3aR^*,5S^*,6aR^*)-3-(phenylmethyl)-2-oxo-3,3a,4,5,6,6a-hexahydro-5-<1-<<(triisopropylsilyl)oxy>methyl>propenyl>-6a-<1-<2-(trimethylacetamido)phenyl>ethenyl>-2H-cyclopentoxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (E,3aR^*,5S^*,6aR^*)-3-(phenylmethyl)-2-oxo-3,3a,4,5,6,6a-hexahydro-5-<1-<<(triisopropylsilyl)oxy>methyl>propenyl>-6a-<1-<2-(trimethylacetamido)phenyl>ethenyl>-2H-cyclopentoxazole

There total 17 articles about (E,3aR^*,5S^*,6aR^*)-3-(phenylmethyl)-2-oxo-3,3a,4,5,6,6a-hexahydro-5-<1-<<(triisopropylsilyl)oxy>methyl>propenyl>-6a-<1-<2-(trimethylacetamido)phenyl>ethenyl>-2H-cyclopentoxazole 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:

triisopropylsilyl chloride (13154-24-0) → (E,3aR*,5S*,6aR*)-3-(phenylmethyl)-2-oxo-3,3a,4,5,6,6a-hexahydro-5-<1-<<(triisopropylsilyl)oxy>methyl>propenyl>-6a-<1-<2-(trimethylacetamido)phenyl>ethenyl>-2H-cyclopentoxazole (97552-32-4)

Guidance literature:

Multi-step reaction with 6 steps

1: imidazole / dimethylformamide / 4.3 h / Ambient temperature

2: 1.) trimethylaluminum, 3.) NaF

3: triethylamine / CH₂Cl₂ / 1 h / 0 °C

4: 1.) oxalyl chloride, dimethylsulfoxide, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C, 10 min

5: 1.) n-BuLi / 1.) hexane, THF, -78 deg C, 40 min, 2.) hexane, THF, -78 deg C, 30 min

6: 1.) n-BuLi / 1.) hexane, THF, from -78 deg C to RT, 15 min, 2.) hexane, THF, from -78 deg C to RT, 64 h

With 1H-imidazole; n-butyllithium; oxalyl dichloride; trimethylaluminum; sodium fluoride; dimethyl sulfoxide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00221a012

Reference yield:

ethyl 2-(3-cyclopentenyl)-2(E)-butenoate (97552-23-3) → (E,3aR*,5S*,6aR*)-3-(phenylmethyl)-2-oxo-3,3a,4,5,6,6a-hexahydro-5-<1-<<(triisopropylsilyl)oxy>methyl>propenyl>-6a-<1-<2-(trimethylacetamido)phenyl>ethenyl>-2H-cyclopentoxazole (97552-32-4)

Guidance literature:

Multi-step reaction with 8 steps

1: m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 0.5 h / 0 °C

2: 78 percent / diisobutylaluminum hydride / toluene / 0.17 h / -78 °C

3: imidazole / dimethylformamide / 4.3 h / Ambient temperature

4: 1.) trimethylaluminum, 3.) NaF

5: triethylamine / CH₂Cl₂ / 1 h / 0 °C

6: 1.) oxalyl chloride, dimethylsulfoxide, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C, 10 min

7: 1.) n-BuLi / 1.) hexane, THF, -78 deg C, 40 min, 2.) hexane, THF, -78 deg C, 30 min

8: 1.) n-BuLi / 1.) hexane, THF, from -78 deg C to RT, 15 min, 2.) hexane, THF, from -78 deg C to RT, 64 h

With 1H-imidazole; n-butyllithium; oxalyl dichloride; trimethylaluminum; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium fluoride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00221a012

Reference yield:

N-(2-bromophenyl)-2,2-dimethylpropanamide (65854-92-4) → (E,3aR*,5S*,6aR*)-3-(phenylmethyl)-2-oxo-3,3a,4,5,6,6a-hexahydro-5-<1-<<(triisopropylsilyl)oxy>methyl>propenyl>-6a-<1-<2-(trimethylacetamido)phenyl>ethenyl>-2H-cyclopentoxazole (97552-32-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) MeLi, 2.) n-BuLi

2: 73 percent / KCN, 18-crowm-6 / CHCl₃ / 0.5 h / Ambient temperature

3: 1.) n-BuLi / 1.) hexane, THF, -78 deg C, 40 min, 2.) hexane, THF, -78 deg C, 30 min

4: 1.) n-BuLi / 1.) hexane, THF, from -78 deg C to RT, 15 min, 2.) hexane, THF, from -78 deg C to RT, 64 h

With potassium cyanide; n-butyllithium; 18-crown-6 ether; methyllithium; In chloroform;

DOI:10.1021/jo00221a012

upstream raw materials:

Methyltriphenylphosphonium bromide

(E,3aR^*,5S^*,6aS^*)-3-(phenylmethyl)-2-oxo-3,3a,4,5,6,6a-hexahydro-5-<1-<<(triisopropylsilyl)oxy>methyl>propenyl>-6a-<2-(trimethylacetamido)benzoyl>-2H-cyclopentoxazole

triisopropylsilyl chloride

ethyl 2-(3-cyclopentenyl)-2(E)-butenoate

Downstream raw materials:

(1S,2S,4R)-1-[1-(2-Amino-phenyl)-vinyl]-2-benzylamino-4-((E)-1-hydroxymethyl-propenyl)-cyclopentanol

(E,3aR^*,5S^*,11bS^*)-5-<1-(hydroxymethyl)propenyl>-2,3,3a,4,5,6-hexahydro-3-(phenylmethyl)-1H-pyrrolo<2,3-d>carbazole

(E,3aR^*,5R^*,6aS^*)-6a-<1-<2-aminophenyl>ethenyl>-5-<1-(hydroxymethyl)propenyl>-3-(phenylmethyl)-3,3a,4,5,6,6a-hexahydro-2H-cyclopentoxazole

(E,3aR^*,5R^*,11bR^*)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-3-(phenylmethyl)-2,3,3a,4,5,6,6a,7-octahydro-1H-pyrrolo<2,3-d>carbazole

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