(4S,6R)-6-Benzyl-4-hydroxy-4-((R)-methoxy-phenyl-methyl)-[1,3]oxazinan-2-one

Base Information

• Chemical Name: (4S,6R)-6-Benzyl-4-hydroxy-4-((R)-methoxy-phenyl-methyl)-[1,3]oxazinan-2-one
• CAS No.: 101693-99-6
• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.38
• Mol file: 101693-99-6.mol

Synonyms:(4S,6R)-6-Benzyl-4-hydroxy-4-((R)-methoxy-phenyl-methyl)-[1,3]oxazinan-2-one

Chemical Property of (4S,6R)-6-Benzyl-4-hydroxy-4-((R)-methoxy-phenyl-methyl)-[1,3]oxazinan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,6R)-6-Benzyl-4-hydroxy-4-((R)-methoxy-phenyl-methyl)-[1,3]oxazinan-2-one

There total 28 articles about (4S,6R)-6-Benzyl-4-hydroxy-4-((R)-methoxy-phenyl-methyl)-[1,3]oxazinan-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: 15.0%

Carbonic acid (1R,4R)-1-benzyl-4-methoxy-3-oxo-4-phenyl-butyl ester 4-nitro-phenyl ester → (4S,6R)-6-Benzyl-4-hydroxy-4-((R)-methoxy-phenyl-methyl)-[1,3]oxazinan-2-one (101693-99-6) + Carbamic acid (R)-1-benzyl-4-methoxy-3-oxo-4-phenyl-butyl ester

Guidance literature:

With ammonia; In methanol; dichloromethane; at -78 - -20 ℃; for 1h;

DOI:10.1016/S0040-4039(01)80069-1

Reference yield:

methyl (R)-(-)-2-methoxy-2-phenylacetate (32174-46-2) → (4S,6R)-6-Benzyl-4-hydroxy-4-((R)-methoxy-phenyl-methyl)-[1,3]oxazinan-2-one (101693-99-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) DIBAL, 2.) NH₂OH / 1.) CH₂Cl₂, -78 deg C to -30 deg C, 2 h, 2.) EtOH, RT, 1.5 h

2: Chlorox, NEt₃ / CH₂Cl₂ / 1 h / Ambient temperature

3: Raney Ni / methanol; H₂O; acetic acid / 16 h / Ambient temperature

4: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

5: NH₃ / methanol; CH₂Cl₂ / 1 h / -78 - -20 °C

With pyridine; sodium hypochlorite; ammonia; hydroxylamine; diisobutylaluminium hydride; triethylamine; nickel; In methanol; dichloromethane; water; acetic acid;

DOI:10.1016/S0040-4039(01)80069-1

Reference yield:

O-methylmandelaldehyde oxime (101693-97-4) → (4S,6R)-6-Benzyl-4-hydroxy-4-((R)-methoxy-phenyl-methyl)-[1,3]oxazinan-2-one (101693-99-6)

Guidance literature:

Multi-step reaction with 4 steps

1: Chlorox, NEt₃ / CH₂Cl₂ / 1 h / Ambient temperature

2: Raney Ni / methanol; H₂O; acetic acid / 16 h / Ambient temperature

3: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

4: NH₃ / methanol; CH₂Cl₂ / 1 h / -78 - -20 °C

With pyridine; sodium hypochlorite; ammonia; triethylamine; nickel; In methanol; dichloromethane; water; acetic acid;

DOI:10.1016/S0040-4039(01)80069-1

upstream raw materials:

allylbenzene

methyl (R)-(-)-2-methoxy-2-phenylacetate

O-methylmandelaldehyde oxime

5-Benzyl-3-((R)-methoxy-phenyl-methyl)-4,5-dihydro-isoxazole