(2S,5R,6R)-6-Allyloxycarbonylamino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,5R,6R)-6-Allyloxycarbonylamino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester
• CAS No.: 211623-32-4
• Molecular Formula: C₁₉H₂₂N₂O₅S
• Molecular Weight: 390.46
• Mol file: 211623-32-4.mol

Synonyms:(2S,5R,6R)-6-Allyloxycarbonylamino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Chemical Property of (2S,5R,6R)-6-Allyloxycarbonylamino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R,6R)-6-Allyloxycarbonylamino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

There total 1 articles about (2S,5R,6R)-6-Allyloxycarbonylamino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl 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:

benzyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (3956-31-8,49626-54-2,64519-71-7) + Allyl chloroformate (2937-50-0) → (2S,5R,6R)-6-Allyloxycarbonylamino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (211623-32-4)

Guidance literature:

With pyridine;

DOI:10.1021/ja980195z

Reference yield:

(2S,5R,6R)-6-Allyloxycarbonylamino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (211623-32-4) → (3R,9R,11R,12S)-9-Methyl-2,6-dioxo-4-phenylacetyl-7-oxa-10-thia-1,4-diaza-tricyclo[7.2.1.03,11]dodecane-12-carboxylic acid

Guidance literature:

Multi-step reaction with 5 steps

1: MCPBA

2: 100 percent / toluene / Heating

3: 1.) AgOAc, 2.) Pd(PPh₃)4, Bu₃SnH, 3.) NaHCO₃

4: Et₃N

5: H₂ / Pd/C / dioxane

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; tri-n-butyl-tin hydride; silver(I) acetate; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In 1,4-dioxane; toluene;

DOI:10.1021/ja980195z

Reference yield:

(2S,5R,6R)-6-Allyloxycarbonylamino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (211623-32-4) → (3R,9R,11R,12S)-9-Methyl-2,6-dioxo-4-phenylcarbamoyl-7-oxa-10-thia-1,4-diaza-tricyclo[7.2.1.03,11]dodecane-12-carboxylic acid

Guidance literature:

Multi-step reaction with 5 steps

1: MCPBA

2: 100 percent / toluene / Heating

3: 1.) AgOAc, 2.) Pd(PPh₃)4, Bu₃SnH, 3.) NaHCO₃

5: H₂ / Pd/C / dioxane

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; tri-n-butyl-tin hydride; silver(I) acetate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In 1,4-dioxane; toluene;

DOI:10.1021/ja980195z

upstream raw materials:

benzyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Allyl chloroformate

Downstream raw materials:

(2S,4S,5R,6R)-6-Allyloxycarbonylamino-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

(3R,9R,11R,12S)-9-Methyl-2,6-dioxo-7-oxa-10-thia-1,4-diaza-tricyclo[7.2.1.0^3,11]dodecane-12-carboxylic acid benzyl ester

(R)-2-[(2R,3R)-3-Allyloxycarbonylamino-2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester