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

Base Information

• Chemical Name: (E,3aR^*,5R^*,6aS^*)-6a-<(2-aminophenyl)ethenyl>-3-(phenylmethyl)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-3,3a,4,5,6,6a-hexahydro-2H-cyclopentoxazole
• CAS No.: 97570-06-4
• Molecular Formula: C₃₁H₄₄N₂O₂Si
• Molecular Weight: 504.788

Synonyms:(E,3aR^*,5R^*,6aS^*)-6a-<(2-aminophenyl)ethenyl>-3-(phenylmethyl)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-3,3a,4,5,6,6a-hexahydro-2H-cyclopentoxazole

Chemical Property of (E,3aR^*,5R^*,6aS^*)-6a-<(2-aminophenyl)ethenyl>-3-(phenylmethyl)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-3,3a,4,5,6,6a-hexahydro-2H-cyclopentoxazole

Chemical Property:

Purity/Quality:

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Technology Process of (E,3aR^*,5R^*,6aS^*)-6a-<(2-aminophenyl)ethenyl>-3-(phenylmethyl)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-3,3a,4,5,6,6a-hexahydro-2H-cyclopentoxazole

There total 18 articles about (E,3aR^*,5R^*,6aS^*)-6a-<(2-aminophenyl)ethenyl>-3-(phenylmethyl)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-3,3a,4,5,6,6a-hexahydro-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: 98.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (E,3aR*,5R*,6aS*)-6a-<1-<2-aminophenyl>ethenyl>-5-<1-(hydroxymethyl)propenyl>-3-(phenylmethyl)-3,3a,4,5,6,6a-hexahydro-2H-cyclopentoxazole (97552-33-5) → (E,3aR*,5R*,6aS*)-6a-<(2-aminophenyl)ethenyl>-3-(phenylmethyl)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-3,3a,4,5,6,6a-hexahydro-2H-cyclopentoxazole (97570-06-4)

Guidance literature:

With dmap; triethylamine; In N,N-dimethyl-formamide; for 2.5h; Ambient temperature;

DOI:10.1021/jo00221a012

Reference yield:

ethyl 2-(3-cyclopentenyl)-2(E)-butenoate (97552-23-3) → (E,3aR*,5R*,6aS*)-6a-<(2-aminophenyl)ethenyl>-3-(phenylmethyl)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-3,3a,4,5,6,6a-hexahydro-2H-cyclopentoxazole (97570-06-4)

Guidance literature:

Multi-step reaction with 11 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

9: 96 percent / KOH / methanol; H₂O / 18 h / Heating

10: 97 percent / tetrahydrofuran / 8 h / Ambient temperature

11: 98 percent / triethylamine, 4-(dimethylamino)pyridine / dimethylformamide / 2.5 h / Ambient temperature

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

DOI:10.1021/jo00221a012

Reference yield:

N-(2-bromophenyl)-2,2-dimethylpropanamide (65854-92-4) → (E,3aR*,5R*,6aS*)-6a-<(2-aminophenyl)ethenyl>-3-(phenylmethyl)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-3,3a,4,5,6,6a-hexahydro-2H-cyclopentoxazole (97570-06-4)

Guidance literature:

Multi-step reaction with 7 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

5: 96 percent / KOH / methanol; H₂O / 18 h / Heating

6: 97 percent / tetrahydrofuran / 8 h / Ambient temperature

7: 98 percent / triethylamine, 4-(dimethylamino)pyridine / dimethylformamide / 2.5 h / Ambient temperature

With dmap; potassium cyanide; potassium hydroxide; n-butyllithium; 18-crown-6 ether; methyllithium; triethylamine; In tetrahydrofuran; methanol; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00221a012

upstream raw materials:

tert-butyldimethylsilyl chloride

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

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

N-(2-formylphenyl)-2,2-dimethylpropionamide

Downstream raw materials:

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

(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

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

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