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

Base Information

Chemical Name:benzyl (3aS,4R,6aR)-2,2-dimethyl-4-{[(2,2,2-trichloroethoxy)carbonyl]amino}-4,6a-dihydro-2H-cyclopenta[d][1,3]oxazole-3(3aH)-carboxylate
CAS No.:947595-48-4
Molecular Formula:C₁₉H₂₁Cl₃N₂O₅
Molecular Weight:463.745
Hs Code.:

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

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

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

There total 7 articles about benzyl (3aS,4R,6aR)-2,2-dimethyl-4-{[(2,2,2-trichloroethoxy)carbonyl]amino}-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: 95.0%

: 947595-47-3
C₁₃H₁₅NO₄C₃H₅NCO

: 115-20-8
1,1,1-trichloroethanol

: 947595-48-4
benzyl (3aS,4R,6aR)-2,2-dimethyl-4-{[(2,2,2-trichloroethoxy)carbonyl]amino}-4,6a-dihydro-2H-cyclopenta[d][1,3]oxazole-3(3aH)-carboxylate

Guidance literature:: C₁₃H₁₅NO₄C₃H₅NCO; With carbon tetrabromide; triethylamine; triphenylphosphine; In dichloromethane; at -10 ℃; for 0.666667h;

1,1,1-trichloroethanol; In dichloromethane; at -10 - 20 ℃; Further stages.;
DOI:10.1021/ol0709735

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

: 947595-48-4
benzyl (3aS,4R,6aR)-2,2-dimethyl-4-{[(2,2,2-trichloroethoxy)carbonyl]amino}-4,6a-dihydro-2H-cyclopenta[d][1,3]oxazole-3(3aH)-carboxylate

Guidance literature:: Multi-step reaction with 6 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

With carbon tetrabromide; Dowex 50W X₈; camphor-10-sulfonic acid; potassium carbonate; triethylamine; triphenylphosphine; Grubbs catalyst first generation; In methanol; dichloromethane; 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

: 947595-48-4
benzyl (3aS,4R,6aR)-2,2-dimethyl-4-{[(2,2,2-trichloroethoxy)carbonyl]amino}-4,6a-dihydro-2H-cyclopenta[d][1,3]oxazole-3(3aH)-carboxylate

Guidance literature:: Multi-step reaction with 5 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

With carbon tetrabromide; camphor-10-sulfonic acid; potassium carbonate; triethylamine; triphenylphosphine; Grubbs catalyst first generation; In methanol; dichloromethane; acetone; benzene;
DOI:10.1021/ol0709735