(2R,5R)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-8-oxo-7-phenyl-3-oxa-1-azabicyclo[3.3.0]oct-6-ene

Base Information

• Chemical Name: (2R,5R)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-8-oxo-7-phenyl-3-oxa-1-azabicyclo[3.3.0]oct-6-ene
• CAS No.: 159970-79-3
• Molecular Formula: C₁₈H₂₁NO₅
• Molecular Weight: 331.368
• Mol file: 159970-79-3.mol

Synonyms:(2R,5R)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-8-oxo-7-phenyl-3-oxa-1-azabicyclo[3.3.0]oct-6-ene

Chemical Property of (2R,5R)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-8-oxo-7-phenyl-3-oxa-1-azabicyclo[3.3.0]oct-6-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5R)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-8-oxo-7-phenyl-3-oxa-1-azabicyclo[3.3.0]oct-6-ene

There total 5 articles about (2R,5R)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-8-oxo-7-phenyl-3-oxa-1-azabicyclo[3.3.0]oct-6-ene 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: 89.0%

methyl (2R,4S,2'SR)-2-(tert-butyl)-3-(2'-ethoxycarbonyl-2'-phenyl)-ethanoyloxazolidine-4-carboxylate → (2R,5R)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-8-oxo-7-phenyl-3-oxa-1-azabicyclo[3.3.0]oct-6-ene (159970-79-3)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; for 3h; Heating;

DOI:10.1055/s-1997-1191

Reference yield:

(2RS,5S)-2-(tert-butyl)-5-methoxycarbonyl-1,3-oxazolidine (190080-34-3) → (2R,5R)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-8-oxo-7-phenyl-3-oxa-1-azabicyclo[3.3.0]oct-6-ene (159970-79-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent

2: 73 percent / t-BuOK / toluene

With potassium tert-butylate; In toluene;

DOI:10.1016/0957-4166(94)80117-7

Reference yield:

2-phenylmalonic acid monoethyl ester (17097-90-4) → (2R,5R)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-8-oxo-7-phenyl-3-oxa-1-azabicyclo[3.3.0]oct-6-ene (159970-79-3)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 6.5 h / 0 - 20 °C

2: potassium tert-butylate / tert-butyl alcohol / 8 h / Reflux

With dmap; potassium tert-butylate; dicyclohexyl-carbodiimide; In dichloromethane; tert-butyl alcohol; 2: |Dieckmann Condensation;

DOI:10.1016/j.tet.2019.130561

upstream raw materials:

(2RS,5S)-2-(tert-butyl)-5-methoxycarbonyl-1,3-oxazolidine

diethyl 2-phenylmalonate

2-phenylmalonic acid monoethyl ester

methyl (2R,4S)-2-(tert-butyl)-1,3-oxazolane-4-carboxylate

Downstream raw materials:

(6bS,9R)-9-tert-Butyl-5-ethoxycarbonylmethyl-10-oxo-10H-8-oxa-9a-aza-pentaleno[2,1-a]naphthalene-6b-carboxylic acid methyl ester

(2R,5R)-2-tert-Butyl-6-hydroxy-8-oxo-7-phenyl-1-aza-3-oxabicyclo[3.3.0]oct-6-ene