(5RS,6RS,7RS)-1-Acetoxy-5-(benzyloxy)-1-azabicyclo<4.3.0>non-3-en-2-one

Base Information

• Chemical Name: (5RS,6RS,7RS)-1-Acetoxy-5-(benzyloxy)-1-azabicyclo<4.3.0>non-3-en-2-one
• CAS No.: 123190-72-7
• Molecular Formula: C₁₇H₁₉NO₄
• Molecular Weight: 301.342
• Mol file: 123190-72-7.mol

Synonyms:(5RS,6RS,7RS)-1-Acetoxy-5-(benzyloxy)-1-azabicyclo<4.3.0>non-3-en-2-one

Chemical Property of (5RS,6RS,7RS)-1-Acetoxy-5-(benzyloxy)-1-azabicyclo<4.3.0>non-3-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5RS,6RS,7RS)-1-Acetoxy-5-(benzyloxy)-1-azabicyclo<4.3.0>non-3-en-2-one

There total 7 articles about (5RS,6RS,7RS)-1-Acetoxy-5-(benzyloxy)-1-azabicyclo<4.3.0>non-3-en-2-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:

acetic anhydride (108-24-7) + (1S,8S,8aR)-8-Benzyloxy-1-hydroxy-2,3,8,8a-tetrahydro-1H-indolizin-5-one → (5RS,6RS,7RS)-1-Acetoxy-5-(benzyloxy)-1-azabicyclo<4.3.0>non-3-en-2-one (123190-72-7)

Guidance literature:

With dmap; In pyridine; at 20 ℃; for 48h; Yield given;

DOI:10.1016/S0040-4039(01)80287-2

Reference yield:

(2R,3R,3aR,6aS)-3-Benzyloxy-2-methoxy-hexahydro-furo[3,2-b]pyrrole (123190-70-5,131724-03-3) → (5RS,6RS,7RS)-1-Acetoxy-5-(benzyloxy)-1-azabicyclo<4.3.0>non-3-en-2-one (123190-72-7)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂ / -5 - 8 °C

2: cc. H₂SO₄ / 2 h / 5 °C

3: 1) (EtO)3P, 2) K₂CO₃ / 1) 130 deg C, 7 h, 2) EtOH, 20 deg C, 12 h

4: 4-dimethylaminopyridine / pyridine / 48 h / 20 °C

With pyridine; dmap; sulfuric acid; potassium carbonate; triethyl phosphite; In pyridine; dichloromethane;

DOI:10.1016/S0040-4039(01)80287-2

Reference yield:

2-((2R,3R,4R,5S)-4-Benzyloxy-3-bromo-5-methoxy-tetrahydro-furan-2-yl)-ethanol (123190-68-1,131635-67-1) → (5RS,6RS,7RS)-1-Acetoxy-5-(benzyloxy)-1-azabicyclo<4.3.0>non-3-en-2-one (123190-72-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / Et₃N / CH₂Cl₂ / 0 °C

2: 12percent NH₃ / ethanol; H₂O / 5 h / 70 °C

3: pyridine / CH₂Cl₂ / -5 - 8 °C

4: cc. H₂SO₄ / 2 h / 5 °C

5: 1) (EtO)3P, 2) K₂CO₃ / 1) 130 deg C, 7 h, 2) EtOH, 20 deg C, 12 h

6: 4-dimethylaminopyridine / pyridine / 48 h / 20 °C

With pyridine; dmap; ammonium hydroxide; sulfuric acid; potassium carbonate; triethylamine; triethyl phosphite; In pyridine; ethanol; dichloromethane; water;

DOI:10.1016/S0040-4039(01)80287-2

upstream raw materials:

acetic anhydride

(2R,3R,3aR,6aS)-3-Benzyloxy-2-methoxy-hexahydro-furo[3,2-b]pyrrole

2-((2R,3R,4R,5S)-4-Benzyloxy-3-bromo-5-methoxy-tetrahydro-furan-2-yl)-ethanol

1-((2R,3R,3aR,6aS)-3-Benzyloxy-2-methoxy-hexahydro-furo[3,2-b]pyrrol-4-yl)-2-chloro-ethanone

Downstream raw materials:

Acetic acid (1R,6S,7R,8S,8aS)-7-acetoxy-8-benzyloxy-6-bromo-5-oxo-octahydro-indolizin-1-yl ester

Acetic acid (1S,6R,7R,8R,8aR)-6-acetoxy-8-benzyloxy-7-bromo-5-oxo-octahydro-indolizin-1-yl ester

(1RS,6RS,7SR,8SR,8aSR)-1-Acetoxy-8-(benzyloxy)-6,7-dibromooctahydroindolizidin-5-one