Acetic acid (1S,7S,10R,11S)-10,11-dihydroxy-3,5-dioxo-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-en-1-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (1S,7S,10R,11S)-10,11-dihydroxy-3,5-dioxo-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-en-1-ylmethyl ester
• CAS No.: 131043-55-5
• Molecular Formula: C₁₇H₁₇N₃O₆
• Molecular Weight: 359.338

Synonyms:Acetic acid (1S,7S,10R,11S)-10,11-dihydroxy-3,5-dioxo-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-en-1-ylmethyl ester

Chemical Property of Acetic acid (1S,7S,10R,11S)-10,11-dihydroxy-3,5-dioxo-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-en-1-ylmethyl ester

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Technology Process of Acetic acid (1S,7S,10R,11S)-10,11-dihydroxy-3,5-dioxo-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-en-1-ylmethyl ester

There total 2 articles about Acetic acid (1S,7S,10R,11S)-10,11-dihydroxy-3,5-dioxo-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-en-1-ylmethyl 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: 43.0%

4-Phenyl-1,2,4-triazolidine-3,5-dione (4233-33-4) + ((5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl)methyl acetate (131043-51-1) → Acetic acid (1S,7S,10R,11S)-10,11-dihydroxy-3,5-dioxo-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.02,6]undec-8-en-1-ylmethyl ester (131043-55-5)

Guidance literature:

In dichloromethane; for 1h; Ambient temperature;

Reference yield:

Benzyl acetate (140-11-4) → Acetic acid (1S,7S,10R,11S)-10,11-dihydroxy-3,5-dioxo-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.02,6]undec-8-en-1-ylmethyl ester (131043-55-5)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene dioxygenase from intact cells of Pseudomonas putida UV₄, O₂

2: 43 percent / CH₂Cl₂ / 1 h / Ambient temperature

With toluene dioxygenase from intact cells of Pseudomonas putida UV₄; oxygen; In dichloromethane;

Reference yield: 100.0%

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4) + Acetic acid (1S,7S,10R,11S)-10,11-dihydroxy-3,5-dioxo-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.02,6]undec-8-en-1-ylmethyl ester (131043-55-5) → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7S,8R,9S)-7-acetoxymethyl-3,5-dioxo-4-phenyl-9-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-2,4,6-triaza-tricyclo[5.2.2.02,6]undec-10-en-8-yl ester (131043-61-3)

Guidance literature:

With pyridine;

DOI:10.1021/ja00002a040

upstream raw materials:

4-Phenyl-1,2,4-triazolidine-3,5-dione

((5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl)methyl acetate

Benzyl acetate

Downstream raw materials:

(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7S,8R,9S)-7-acetoxymethyl-3,5-dioxo-4-phenyl-9-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl ester

(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7S,8R,9S)-7-acetoxymethyl-3,5-dioxo-4-phenyl-9-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl ester

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