Acetic acid (1aS,8R,9S,9aR)-9-hydroxy-8-(2-oxo-2-phenyl-ethyl)-1a,8,9,9a-tetrahydro-2H-1-oxa-3-aza-benzo[a]cyclopropa[e]cycloocten-3-yl ester

Base Information

• Chemical Name: Acetic acid (1aS,8R,9S,9aR)-9-hydroxy-8-(2-oxo-2-phenyl-ethyl)-1a,8,9,9a-tetrahydro-2H-1-oxa-3-aza-benzo[a]cyclopropa[e]cycloocten-3-yl ester
• CAS No.: 127766-73-8
• Molecular Formula: C₂₁H₂₁NO₅
• Molecular Weight: 367.401
• Mol file: 127766-73-8.mol

Synonyms:

Chemical Property of Acetic acid (1aS,8R,9S,9aR)-9-hydroxy-8-(2-oxo-2-phenyl-ethyl)-1a,8,9,9a-tetrahydro-2H-1-oxa-3-aza-benzo[a]cyclopropa[e]cycloocten-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1aS,8R,9S,9aR)-9-hydroxy-8-(2-oxo-2-phenyl-ethyl)-1a,8,9,9a-tetrahydro-2H-1-oxa-3-aza-benzo[a]cyclopropa[e]cycloocten-3-yl ester

There total 17 articles about Acetic acid (1aS,8R,9S,9aR)-9-hydroxy-8-(2-oxo-2-phenyl-ethyl)-1a,8,9,9a-tetrahydro-2H-1-oxa-3-aza-benzo[a]cyclopropa[e]cycloocten-3-yl 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: 78.0%

Acetic acid (Z)-(5S,6S)-5-hydroxy-6-(2-oxo-2-phenyl-ethyl)-5,6-dihydro-2H-benzo[b]azocin-1-yl ester (127766-72-7,133099-16-8) → Acetic acid (1aS,8R,9S,9aR)-9-hydroxy-8-(2-oxo-2-phenyl-ethyl)-1a,8,9,9a-tetrahydro-2H-1-oxa-3-aza-benzo[a]cyclopropa[e]cycloocten-3-yl ester (127766-73-8,133099-17-9)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 23 ℃;

DOI:10.1016/S0040-4039(01)89002-X

Reference yield:

2-Aminobenzyl alcohol (5344-90-1) → Acetic acid (1aS,8R,9S,9aR)-9-hydroxy-8-(2-oxo-2-phenyl-ethyl)-1a,8,9,9a-tetrahydro-2H-1-oxa-3-aza-benzo[a]cyclopropa[e]cycloocten-3-yl ester (127766-73-8,133099-17-9)

Guidance literature:

Multi-step reaction with 17 steps

1: HNO₂, NaN₃

2: PCC

3: NaOH

4: 100 percent / n-Bu₄NF / tetrahydrofuran / -78 °C

5: 85 percent / BF₃-Et₂O / CH₂Cl₂

6: 81 percent / ethanol

7: 91 percent / Ph₃P, AcOH / methanol; tetrahydrofuran / 23 °C

8: 1.) DIBAL, 2.) NaBH₃CN, TFA / 1.) CH₂Cl₂, -78 deg C, 2.) MeOH, CH₂Cl₂

9: pyridine / CH₂Cl₂

10: pyridine

11: 99 percent / HgCl₂ / methanol / Heating

12: MCPBA / CH₂Cl₂

13: toluene / 175 °C

14: 70 percent / NaOH/H₂O / methanol / Heating

15: 89 percent / 2-(phenylsulfonyl)-3-phenyloxaziridine (Davis' reagent) / tetrahydrofuran / 23 °C

16: 85 percent / 23 °C

17: 78 percent / MCPBA, NaHCO₃ / CH₂Cl₂ / 23 °C

With pyridine; sodium hydroxide; sodium azide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; cis-nitrous acid; diisobutylaluminium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; N-(benzenesulfonyl)-3-phenyloxaziridine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; mercury dichloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene;

DOI:10.1016/S0040-4039(01)89002-X

Reference yield:

(E)-3-(2-azidophenyl)-1-phenylprop-2-en-1-one (33037-74-0) → Acetic acid (1aS,8R,9S,9aR)-9-hydroxy-8-(2-oxo-2-phenyl-ethyl)-1a,8,9,9a-tetrahydro-2H-1-oxa-3-aza-benzo[a]cyclopropa[e]cycloocten-3-yl ester (127766-73-8,133099-17-9)

Guidance literature:

Multi-step reaction with 14 steps

1: 100 percent / n-Bu₄NF / tetrahydrofuran / -78 °C

2: 85 percent / BF₃-Et₂O / CH₂Cl₂

3: 81 percent / ethanol

4: 91 percent / Ph₃P, AcOH / methanol; tetrahydrofuran / 23 °C

5: 1.) DIBAL, 2.) NaBH₃CN, TFA / 1.) CH₂Cl₂, -78 deg C, 2.) MeOH, CH₂Cl₂

6: pyridine / CH₂Cl₂

7: pyridine

8: 99 percent / HgCl₂ / methanol / Heating

9: MCPBA / CH₂Cl₂

10: toluene / 175 °C

11: 70 percent / NaOH/H₂O / methanol / Heating

12: 89 percent / 2-(phenylsulfonyl)-3-phenyloxaziridine (Davis' reagent) / tetrahydrofuran / 23 °C

13: 85 percent / 23 °C

14: 78 percent / MCPBA, NaHCO₃ / CH₂Cl₂ / 23 °C

With pyridine; sodium hydroxide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; N-(benzenesulfonyl)-3-phenyloxaziridine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic acid; mercury dichloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene;

DOI:10.1016/S0040-4039(01)89002-X

upstream raw materials:

Acetic acid (Z)-(5S,6S)-5-hydroxy-6-(2-oxo-2-phenyl-ethyl)-5,6-dihydro-2H-benzo[b]azocin-1-yl ester

2-Aminobenzyl alcohol

(E)-3-(2-azidophenyl)-1-phenylprop-2-en-1-one

2-azidobenzyl alcohol

Downstream raw materials:

C₁₉H₁₅NO₃

C₁₉H₁₇NO₄