(6R,7R)-3-(2-Acetoxy-benzoyloxymethyl)-7-tert-butoxycarbonylamino-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (6R,7R)-3-(2-Acetoxy-benzoyloxymethyl)-7-tert-butoxycarbonylamino-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
• CAS No.: 219901-35-6
• Molecular Formula: C₂₆H₃₂N₂O₁₁S
• Molecular Weight: 580.613

Synonyms:

Chemical Property of (6R,7R)-3-(2-Acetoxy-benzoyloxymethyl)-7-tert-butoxycarbonylamino-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (6R,7R)-3-(2-Acetoxy-benzoyloxymethyl)-7-tert-butoxycarbonylamino-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

There total 1 articles about (6R,7R)-3-(2-Acetoxy-benzoyloxymethyl)-7-tert-butoxycarbonylamino-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl 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:

(2R,6R,7R)-7-tert-Butoxycarbonylamino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid tert-butyl ester (219901-34-5) + O-acetylsalicyloyl chloride (5538-51-2) → (6R,7R)-3-(2-Acetoxy-benzoyloxymethyl)-7-tert-butoxycarbonylamino-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (219901-35-6)

Guidance literature:

With dihydrogen peroxide; triethylamine; sodium tungstate; Yield given. Multistep reaction; 1) CH₂Cl₂, r.t., 24 h, 2) acetonitrile, r.t., 24 h;

DOI:10.1016/S0223-5234(99)80027-0

Reference yield: 38.0%

trifluoroacetic acid (76-05-1) + (6R,7R)-3-(2-Acetoxy-benzoyloxymethyl)-7-tert-butoxycarbonylamino-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (219901-35-6) → (6R,7R)-3-(2-Acetoxy-benzoyloxymethyl)-7-amino-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester; compound with trifluoro-acetic acid

Guidance literature:

for 0.116667h; Ambient temperature;

DOI:10.1016/S0223-5234(99)80027-0

Reference yield:

(6R,7R)-3-(2-Acetoxy-benzoyloxymethyl)-7-tert-butoxycarbonylamino-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (219901-35-6) → (6R,7S)-3-(2-Acetoxy-benzoyloxymethyl)-7-methoxy-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 38 percent / 0.12 h / Ambient temperature

2: i-PrONO / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 27 percent / Rh₂(OAc)4

With i-propyl nitrite; dirhodium tetraacetate; In dichloromethane;

DOI:10.1016/S0223-5234(99)80027-0

upstream raw materials:

(2R,6R,7R)-7-tert-Butoxycarbonylamino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid tert-butyl ester

O-acetylsalicyloyl chloride

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