phenyl[(1R,2S,6S,7R)-4,4,7-trimethyl-3,5,8-trioxa-9-azatricyclo[5.2.2.0^2,6]undec-10-en-9-yl]methanone

Base Information

• Chemical Name: phenyl[(1R,2S,6S,7R)-4,4,7-trimethyl-3,5,8-trioxa-9-azatricyclo[5.2.2.0^2,6]undec-10-en-9-yl]methanone
• CAS No.: 278600-83-2
• Molecular Formula: C₁₇H₁₉NO₄
• Molecular Weight: 301.342

Synonyms:phenyl[(1R,2S,6S,7R)-4,4,7-trimethyl-3,5,8-trioxa-9-azatricyclo[5.2.2.0^2,6]undec-10-en-9-yl]methanone

Chemical Property of phenyl[(1R,2S,6S,7R)-4,4,7-trimethyl-3,5,8-trioxa-9-azatricyclo[5.2.2.0^2,6]undec-10-en-9-yl]methanone

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of phenyl[(1R,2S,6S,7R)-4,4,7-trimethyl-3,5,8-trioxa-9-azatricyclo[5.2.2.0^2,6]undec-10-en-9-yl]methanone

There total 3 articles about phenyl[(1R,2S,6S,7R)-4,4,7-trimethyl-3,5,8-trioxa-9-azatricyclo[5.2.2.0^2,6]undec-10-en-9-yl]methanone 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: 88.0%

Benzohydroxamic acid (495-18-1) + (3aR,7aS)-2,2,4-trimethyl-3a,7a-dihydro-1,3-benzodioxole (114763-30-3) → phenyl[(1R,2S,6S,7R)-4,4,7-trimethyl-3,5,8-trioxa-9-azatricyclo[5.2.2.02,6]undec-10-en-9-yl]methanone (278600-83-2)

Guidance literature:

With benzyltrimethylammonium periodate; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 2h;

DOI:10.1021/ol000057q

Reference yield:

(2R,3S)-2,3-dihydroxy-1-methylcyclohexa-4,6-diene (41977-20-2) → phenyl[(1R,2S,6S,7R)-4,4,7-trimethyl-3,5,8-trioxa-9-azatricyclo[5.2.2.02,6]undec-10-en-9-yl]methanone (278600-83-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent

2: 88 percent / benzyltrimethylammonium periodate / dimethylformamide; CH₂Cl₂ / 2 h / 0 °C

With benzyltrimethylammonium periodate; In dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Diels-Alder cycloaddition;

DOI:10.1021/ol000057q

Reference yield:

toluene (108-88-3,15644-74-3,16713-13-6) → phenyl[(1R,2S,6S,7R)-4,4,7-trimethyl-3,5,8-trioxa-9-azatricyclo[5.2.2.02,6]undec-10-en-9-yl]methanone (278600-83-2)

Guidance literature:

Multi-step reaction with 3 steps

1: Pseudomonas putida UV₄; O₂

2: 95 percent

3: 88 percent / benzyltrimethylammonium periodate / dimethylformamide; CH₂Cl₂ / 2 h / 0 °C

With Pseudomonas putida UV₄; oxygen; benzyltrimethylammonium periodate; In dichloromethane; N,N-dimethyl-formamide; 1: Enzymatic cis-dihydroxylation / 2: Etherification / 3: Diels-Alder cycloaddition;

DOI:10.1021/ol000057q

upstream raw materials:

Benzohydroxamic acid

(3aR,7aS)-2,2,4-trimethyl-3a,7a-dihydro-1,3-benzodioxole

(2R,3S)-2,3-dihydroxy-1-methylcyclohexa-4,6-diene

toluene

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