(1S,4S,5R)-4-benzyloxycarbonylamino-2-oxabicyclo[3.3.0]oct-7-ene-3-one

Base Information

• Chemical Name: (1S,4S,5R)-4-benzyloxycarbonylamino-2-oxabicyclo[3.3.0]oct-7-ene-3-one
• CAS No.: 174742-31-5
• Molecular Formula: C₁₅H₁₅NO₄
• Molecular Weight: 273.288
• Mol file: 174742-31-5.mol

Synonyms:(1S,4S,5R)-4-benzyloxycarbonylamino-2-oxabicyclo[3.3.0]oct-7-ene-3-one

Chemical Property of (1S,4S,5R)-4-benzyloxycarbonylamino-2-oxabicyclo[3.3.0]oct-7-ene-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S,5R)-4-benzyloxycarbonylamino-2-oxabicyclo[3.3.0]oct-7-ene-3-one

There total 10 articles about (1S,4S,5R)-4-benzyloxycarbonylamino-2-oxabicyclo[3.3.0]oct-7-ene-3-one 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: 94.0%

benzyl chloroformate (501-53-1,94274-21-2) + (-)-4-endo-Amino-2-oxabicyclo[3.3.0]oct-7-en-3-one (174742-36-0) → (1S,4S,5R)-4-benzyloxycarbonylamino-2-oxabicyclo[3.3.0]oct-7-ene-3-one (174742-31-5)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) + (3S,3aR,6aR)-3-Amino-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one; compound with toluene-4-sulfonic acid → (1S,4S,5R)-4-benzyloxycarbonylamino-2-oxabicyclo[3.3.0]oct-7-ene-3-one (174742-31-5)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo000903a

Reference yield:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1S,4S,5R)-4-benzyloxycarbonylamino-2-oxabicyclo[3.3.0]oct-7-ene-3-one (174742-31-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 76 percent / benzene / 4 h / 20 °C

2.1: Mo(CO)6 / acetonitrile; H₂O / 2 h / Heating

2.2: 68 percent / acetonitrile; H₂O / 10 h / 20 °C

3.1: CH₂Cl₂ / 40 °C

4.1: 98.0 mg / aq. NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

With hexacarbonyl molybdenum; sodium hydrogencarbonate; In dichloromethane; water; acetonitrile; benzene;

DOI:10.1021/jo000903a

upstream raw materials:

benzyl chloroformate

(3S,3aR,6aR)-3-hydroxy-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one

(-)-4-endo-Amino-2-oxabicyclo[3.3.0]oct-7-en-3-one

cyclopenta-1,3-diene

Downstream raw materials:

(S)-Benzyloxycarbonylamino-[(1S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopent-2-enyl]-acetic acid

(S)-((1S,4R)-4-Azido-cyclopent-2-enyl)-benzyloxycarbonylamino-acetic acid

(S)-Benzyloxycarbonylamino-[(1R,2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,3-dihydroxy-cyclopentyl]-acetic acid benzyl ester

(S)-Benzyloxycarbonylamino-[(1S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopent-2-enyl]-acetic acid benzyl ester