benzyl (3aS,4R,6aR)-4-{[(4,5-dibromo-1H-pyrrol-2-yl)carbonyl]amino}-2,2-dimethyl-4,6a-dihydro-2H-cyclopenta[d][1,3]oxazole-3(3aH)-carboxylate

Base Information

Chemical Name:benzyl (3aS,4R,6aR)-4-{[(4,5-dibromo-1H-pyrrol-2-yl)carbonyl]amino}-2,2-dimethyl-4,6a-dihydro-2H-cyclopenta[d][1,3]oxazole-3(3aH)-carboxylate
CAS No.:947595-49-5
Molecular Formula:C₂₁H₂₁Br₂N₃O₄
Molecular Weight:539.223
Hs Code.:

Synonyms:benzyl (3aS,4R,6aR)-4-{[(4,5-dibromo-1H-pyrrol-2-yl)carbonyl]amino}-2,2-dimethyl-4,6a-dihydro-2H-cyclopenta[d][1,3]oxazole-3(3aH)-carboxylate

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Chemical Property of benzyl (3aS,4R,6aR)-4-{[(4,5-dibromo-1H-pyrrol-2-yl)carbonyl]amino}-2,2-dimethyl-4,6a-dihydro-2H-cyclopenta[d][1,3]oxazole-3(3aH)-carboxylate

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Technology Process of benzyl (3aS,4R,6aR)-4-{[(4,5-dibromo-1H-pyrrol-2-yl)carbonyl]amino}-2,2-dimethyl-4,6a-dihydro-2H-cyclopenta[d][1,3]oxazole-3(3aH)-carboxylate

There total 9 articles about benzyl (3aS,4R,6aR)-4-{[(4,5-dibromo-1H-pyrrol-2-yl)carbonyl]amino}-2,2-dimethyl-4,6a-dihydro-2H-cyclopenta[d][1,3]oxazole-3(3aH)-carboxylate 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:

: 947595-45-1
benzyl {(1S,2E)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]pent-2-en-1-yl}carbamate

: 947595-49-5
benzyl (3aS,4R,6aR)-4-{[(4,5-dibromo-1H-pyrrol-2-yl)carbonyl]amino}-2,2-dimethyl-4,6a-dihydro-2H-cyclopenta[d][1,3]oxazole-3(3aH)-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 92 percent / Dowex 50W x8 / methanol / 26 h / Heating

2.1: 83 percent / (PCy₃)2Cl₂Ru=CHPh / benzene / 15 h / 60 °C

3.1: CSA / acetone / 6 h / 20 °C

3.2: 99 percent / H₂O; silica gel / CH₂Cl₂ / 7 h / 20 °C

4.1: CH₂Cl₂ / 0.5 h / 0 °C

5.1: 111 mg / aq. K₂CO₃ / methanol / 7 h / 20 °C

6.1: PPh₃; CBr₄; Et₃N / CH₂Cl₂ / 0.67 h / -10 °C

6.2: 95 percent / CH₂Cl₂ / -10 - 20 °C

7.1: Zn; AcOH / tetrahydrofuran / 3 h / 20 °C

8.1: 221 mg / Na₂CO₃ / dimethylformamide / 15.5 h / 20 °C

With carbon tetrabromide; Dowex 50W X₈; camphor-10-sulfonic acid; sodium carbonate; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; zinc; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/ol0709735

Reference yield:

: 947595-38-2
benzyl {(1S,2E)-1-[(1S,2S)-1,2-dihydroxybut-3-en-1-yl]pent-2-en-1-yl}carbamate

: 947595-49-5
benzyl (3aS,4R,6aR)-4-{[(4,5-dibromo-1H-pyrrol-2-yl)carbonyl]amino}-2,2-dimethyl-4,6a-dihydro-2H-cyclopenta[d][1,3]oxazole-3(3aH)-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 83 percent / (PCy₃)2Cl₂Ru=CHPh / benzene / 15 h / 60 °C

2.1: CSA / acetone / 6 h / 20 °C

2.2: 99 percent / H₂O; silica gel / CH₂Cl₂ / 7 h / 20 °C

3.1: CH₂Cl₂ / 0.5 h / 0 °C

4.1: 111 mg / aq. K₂CO₃ / methanol / 7 h / 20 °C

5.1: PPh₃; CBr₄; Et₃N / CH₂Cl₂ / 0.67 h / -10 °C

5.2: 95 percent / CH₂Cl₂ / -10 - 20 °C

6.1: Zn; AcOH / tetrahydrofuran / 3 h / 20 °C

7.1: 221 mg / Na₂CO₃ / dimethylformamide / 15.5 h / 20 °C

With carbon tetrabromide; camphor-10-sulfonic acid; sodium carbonate; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; zinc; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/ol0709735

Reference yield:

: 33868-53-0
tributylstannyl benzyl ether

: 947595-49-5
benzyl (3aS,4R,6aR)-4-{[(4,5-dibromo-1H-pyrrol-2-yl)carbonyl]amino}-2,2-dimethyl-4,6a-dihydro-2H-cyclopenta[d][1,3]oxazole-3(3aH)-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: PPh₃; CBr₄; Et₃N / CH₂Cl₂ / 1.5 h / -10 °C

1.2: CH₂Cl₂ / -10 - 20 °C

1.3: 706 mg / KF / acetonitrile / 24 h / 20 °C

2.1: 92 percent / Dowex 50W x8 / methanol / 26 h / Heating

3.1: 83 percent / (PCy₃)2Cl₂Ru=CHPh / benzene / 15 h / 60 °C

4.1: CSA / acetone / 6 h / 20 °C

4.2: 99 percent / H₂O; silica gel / CH₂Cl₂ / 7 h / 20 °C

5.1: CH₂Cl₂ / 0.5 h / 0 °C

6.1: 111 mg / aq. K₂CO₃ / methanol / 7 h / 20 °C

7.1: PPh₃; CBr₄; Et₃N / CH₂Cl₂ / 0.67 h / -10 °C

7.2: 95 percent / CH₂Cl₂ / -10 - 20 °C

8.1: Zn; AcOH / tetrahydrofuran / 3 h / 20 °C

9.1: 221 mg / Na₂CO₃ / dimethylformamide / 15.5 h / 20 °C

With carbon tetrabromide; Dowex 50W X₈; camphor-10-sulfonic acid; sodium carbonate; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; zinc; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/ol0709735