(2S,3S)-3-bromo-4-hydroxy-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

Base Information

• Chemical Name: (2S,3S)-3-bromo-4-hydroxy-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
• CAS No.: 68539-37-7
• Molecular Formula: C₂₈H₂₅BrN₂O₅
• Molecular Weight: 549.421
• Mol file: 68539-37-7.mol

Synonyms:

Chemical Property of (2S,3S)-3-bromo-4-hydroxy-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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-bromo-4-hydroxy-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

There total 1 articles about (2S,3S)-3-bromo-4-hydroxy-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 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:

epi-Secopenicillin (67977-61-1,68107-98-2) → (2R,3Ξ)-4-bromo-3-hydroxy-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 (73786-40-0,73804-09-8) + (2S,3S)-3-bromo-4-hydroxy-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 (68539-37-7)

Guidance literature:

With N-Bromosuccinimide; In water; acetone; at 15 ℃;

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

Reference yield:

(2S,3S)-3-bromo-4-hydroxy-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 (68539-37-7) → (6R)-7c-benzoylamino-3t-bromo-3c-methyl-8-oxo-(6rH)-5-oxa-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid benzhydryl ester (73786-37-5,73804-31-6,74183-10-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; ethyl acetate; at 25 ℃;

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

Reference yield:

(2S,3S)-3-bromo-4-hydroxy-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 (68539-37-7) → (6R)-7t-amino-7c-methoxy-3-methyl-8-oxo-(6rH)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (77982-90-2)

Guidance literature:

Multi-step reaction with 4 steps

1: BF₃-Et₂O / ethyl acetate; CH₂Cl₂ / 25 °C

2: DBU / CH₂Cl₂ / -20 °C

3: tBuOCl / CH₂Cl₂ / -40 °C

4: PCl₅, Py / CH₂Cl₂ / 25 °C

With pyridine; tert-butylhypochlorite; phosphorus pentachloride; boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; ethyl acetate;

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

upstream raw materials:

epi-Secopenicillin

Downstream raw materials:

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

(6R)-7t-amino-7c-methoxy-3-methyl-8-oxo-(6rH)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

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

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