benzyl (4S,8S,9R,10S)-1-aza-10-[(R)-1-hydroxyethyl]-11-oxo-4-[(formyl)(methyl)amino]tricyclo[7.2.0.0^3,8]undec-2-ene-2-carboxylate

Base Information

• Chemical Name: benzyl (4S,8S,9R,10S)-1-aza-10-[(R)-1-hydroxyethyl]-11-oxo-4-[(formyl)(methyl)amino]tricyclo[7.2.0.0^3,8]undec-2-ene-2-carboxylate
• CAS No.: 246546-99-6
• Molecular Formula: C₂₂H₂₆N₂O₅
• Molecular Weight: 398.459

Synonyms:benzyl (4S,8S,9R,10S)-1-aza-10-[(R)-1-hydroxyethyl]-11-oxo-4-[(formyl)(methyl)amino]tricyclo[7.2.0.0^3,8]undec-2-ene-2-carboxylate

Chemical Property of benzyl (4S,8S,9R,10S)-1-aza-10-[(R)-1-hydroxyethyl]-11-oxo-4-[(formyl)(methyl)amino]tricyclo[7.2.0.0^3,8]undec-2-ene-2-carboxylate

Chemical Property:

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Technology Process of benzyl (4S,8S,9R,10S)-1-aza-10-[(R)-1-hydroxyethyl]-11-oxo-4-[(formyl)(methyl)amino]tricyclo[7.2.0.0^3,8]undec-2-ene-2-carboxylate

There total 7 articles about benzyl (4S,8S,9R,10S)-1-aza-10-[(R)-1-hydroxyethyl]-11-oxo-4-[(formyl)(methyl)amino]tricyclo[7.2.0.0^3,8]undec-2-ene-2-carboxylate 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: 72.0%

benzyl (4S,8S,9R,10S)-1-aza-10-[(R)-1-(trimethylsilyloxy)ethyl]-11-oxo-4-[(formyl)(methyl)amino]tricyclo[7.2.0.03,8]undec-2-ene-2-carboxylate (246546-97-4) → benzyl (4S,8S,9R,10S)-1-aza-10-[(R)-1-hydroxyethyl]-11-oxo-4-[(formyl)(methyl)amino]tricyclo[7.2.0.03,8]undec-2-ene-2-carboxylate (246546-99-6)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 2h;

DOI:10.1007/BF02256813

Reference yield:

benzyl chlorooxalate (35249-73-1) → benzyl (4S,8S,9R,10S)-1-aza-10-[(R)-1-hydroxyethyl]-11-oxo-4-[(formyl)(methyl)amino]tricyclo[7.2.0.03,8]undec-2-ene-2-carboxylate (246546-99-6)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: P(OEt)3 / toluene / 6 h / 110 °C

3: 70 percent / AcOH; TBAF*3H₂O / tetrahydrofuran / 8 h

4: Pd(PPh₃)4 / CH₂Cl₂ / 1 h

5: 60 percent / Et₃N / CH₂Cl₂ / 0.33 h

6: 72 percent / AcOH; TBAF*3H₂O / tetrahydrofuran / 2 h

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; acetic acid; triethylamine; triethyl phosphite; In tetrahydrofuran; dichloromethane; toluene; 1: Acylation / 2: Cyclization / 3: desilylation / 4: silylation / 5: Acylation / 6: desilylation;

DOI:10.1007/BF02256813

Reference yield:

((1S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexyl)-methyl-carbamic acid allyl ester (135297-32-4) → benzyl (4S,8S,9R,10S)-1-aza-10-[(R)-1-hydroxyethyl]-11-oxo-4-[(formyl)(methyl)amino]tricyclo[7.2.0.03,8]undec-2-ene-2-carboxylate (246546-99-6)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: P(OEt)3 / toluene / 6 h / 110 °C

3: 70 percent / AcOH; TBAF*3H₂O / tetrahydrofuran / 8 h

4: Pd(PPh₃)4 / CH₂Cl₂ / 1 h

5: 60 percent / Et₃N / CH₂Cl₂ / 0.33 h

6: 72 percent / AcOH; TBAF*3H₂O / tetrahydrofuran / 2 h

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; acetic acid; triethylamine; triethyl phosphite; In tetrahydrofuran; dichloromethane; toluene; 1: Acylation / 2: Cyclization / 3: desilylation / 4: silylation / 5: Acylation / 6: desilylation;

DOI:10.1007/BF02256813

upstream raw materials:

benzyl (4S,8S,9R,10S)-1-aza-10-[(R)-1-(trimethylsilyloxy)ethyl]-11-oxo-4-[(formyl)(methyl)amino]tricyclo[7.2.0.0^3,8]undec-2-ene-2-carboxylate

benzyl chlorooxalate

((1S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexyl)-methyl-carbamic acid allyl ester

(1S,5S,8aS,8bR)-5-Methylamino-2-oxo-1-((R)-1-trimethylsilanyloxy-ethyl)-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl ester

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