[2R-(2alpha,6alpha,7alpha)]-7-(Benzoylamino)-3-methyl-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid diphenylmethyl ester

Base Information

• Chemical Name: [2R-(2alpha,6alpha,7alpha)]-7-(Benzoylamino)-3-methyl-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid diphenylmethyl ester
• CAS No.: 68314-21-6
• Molecular Formula: C₂₈H₂₄N₂O₅
• Molecular Weight: 468.509
• Mol file: 68314-21-6.mol

Synonyms:[2R-(2a,6a,7a)]-7-(benzoylamino)-3-methyl-8-oxo-5-Oxa-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid diphenylmethyl ester;

Chemical Property of [2R-(2alpha,6alpha,7alpha)]-7-(Benzoylamino)-3-methyl-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid diphenylmethyl ester

Chemical Property:

• PSA: 84.94000
• Density: 1.35
• LogP: 3.91750

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [2R-(2alpha,6alpha,7alpha)]-7-(Benzoylamino)-3-methyl-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid diphenylmethyl ester

There total 3 articles about [2R-(2alpha,6alpha,7alpha)]-7-(Benzoylamino)-3-methyl-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid diphenylmethyl ester 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:

(6R)-7c-benzoylamino-3t-hydroxy-3c-methyl-8-oxo-(6rH)-5-oxa-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid benzhydryl ester (68313-66-6) → (6R)-7c-benzoylamino-3-methyl-8-oxo-(6rH)-5-oxa-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid benzhydryl ester (68314-21-6)

Guidance literature:

With pyridine; thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; at 25 ℃; for 5h;

DOI:10.1016/S0040-4039(01)86579-5

Reference yield:

epi-Secopenicillin (67977-61-1,68107-98-2) → (6R)-7c-benzoylamino-3-methyl-8-oxo-(6rH)-5-oxa-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid benzhydryl ester (68314-21-6)

Guidance literature:

Multi-step reaction with 3 steps

1: KClO₃, OsO₄ / tetrahydrofuran; H₂O / 60 °C

2: BF₃-Et₂O / CH₂Cl₂ / 25 °C

3: SOCl₂, Py / CH₂Cl₂; dimethylformamide / 5 h / 25 °C

With pyridine; osmium(VIII) oxide; thionyl chloride; potassium chlorate; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)86579-5

Reference yield:

(2R,3Ξ)-3,4-dihydroxy-3-methyl-2-((1R)-7-oxo-3-phenyl-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-butyric acid benzhydryl ester (68313-65-5,68539-32-2,68539-33-3) → (6R)-7c-benzoylamino-3-methyl-8-oxo-(6rH)-5-oxa-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid benzhydryl ester (68314-21-6)

Guidance literature:

Multi-step reaction with 2 steps

1: BF₃-Et₂O / CH₂Cl₂ / 25 °C

2: SOCl₂, Py / CH₂Cl₂; dimethylformamide / 5 h / 25 °C

With pyridine; thionyl chloride; boron trifluoride diethyl etherate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)86579-5

upstream raw materials:

(6R)-7c-benzoylamino-3t-hydroxy-3c-methyl-8-oxo-(6rH)-5-oxa-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid benzhydryl ester

epi-Secopenicillin

(2R,3Ξ)-3,4-dihydroxy-3-methyl-2-((1R)-7-oxo-3-phenyl-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-butyric acid benzhydryl ester