dimethyl (1RS,2SR,6RS,7SR,8RS,9RS)-4-phenyl-5,10-dioxa-3-azatricyclo<4.3.1.0^2,7>dec-3-ene-8,9-dicarboxylate

Base Information

• Chemical Name: dimethyl (1RS,2SR,6RS,7SR,8RS,9RS)-4-phenyl-5,10-dioxa-3-azatricyclo<4.3.1.0^2,7>dec-3-ene-8,9-dicarboxylate
• CAS No.: 129814-77-3
• Molecular Formula: C₁₇H₁₇NO₆
• Molecular Weight: 331.325

Synonyms:dimethyl (1RS,2SR,6RS,7SR,8RS,9RS)-4-phenyl-5,10-dioxa-3-azatricyclo<4.3.1.0^2,7>dec-3-ene-8,9-dicarboxylate

Chemical Property of dimethyl (1RS,2SR,6RS,7SR,8RS,9RS)-4-phenyl-5,10-dioxa-3-azatricyclo<4.3.1.0^2,7>dec-3-ene-8,9-dicarboxylate

Chemical Property:

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Technology Process of dimethyl (1RS,2SR,6RS,7SR,8RS,9RS)-4-phenyl-5,10-dioxa-3-azatricyclo<4.3.1.0^2,7>dec-3-ene-8,9-dicarboxylate

There total 6 articles about dimethyl (1RS,2SR,6RS,7SR,8RS,9RS)-4-phenyl-5,10-dioxa-3-azatricyclo<4.3.1.0^2,7>dec-3-ene-8,9-dicarboxylate 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: 94.0%

dimethyl (1RS,2SR,4RS,5SR,6SR,7RS)-3-benzoyl-8-oxa-3-azatricyclo<3.2.1.02,4>octane-6,7-dicarboxylate (129814-71-7,129893-72-7) → dimethyl (1RS,2SR,6RS,7SR,8RS,9RS)-4-phenyl-5,10-dioxa-3-azatricyclo<4.3.1.02,7>dec-3-ene-8,9-dicarboxylate (129814-77-3)

Guidance literature:

With perchloric acid; C₄H₅F₅O; at 20 ℃; for 1h;

DOI:10.1002/hlca.19900730316

Reference yield: 63.0%

dimethyl (1RS,2SR,4RS,5SR,6SR,7RS)-3-benzoyl-8-oxa-3-azatricyclo<3.2.1.02,4>octane-6,7-dicarboxylate (129814-71-7,129893-72-7) + acetic acid (64-19-7,77671-22-8) → dimethyl (1RS,2SR,6RS,7SR,8RS,9RS)-4-phenyl-5,10-dioxa-3-azatricyclo<4.3.1.02,7>dec-3-ene-8,9-dicarboxylate (129814-77-3) + dimethyl (1RS,2RS,3SR,4SR,5SR,6RS)-5-endo-acetoxy-6-exo-(benzoylamino)-7-oxabicyclo<2.2.1>heptane-2-exo,3-exo-dicarboxylate (129814-76-2)

Guidance literature:

With methanesulfonic acid; trifluoromethylsulfonic anhydride; C₄H₅F₅O; at 20 ℃; for 24h;

DOI:10.1002/hlca.19900730316

Reference yield:

dimethyl 7-oxabicyclo[2.2.1]hept-5-ene exo,exo-2,3-dicarboxylate (1984-43-6,6828-11-1,51372-64-6,59275-03-5) → dimethyl (1RS,2SR,6RS,7SR,8RS,9RS)-4-phenyl-5,10-dioxa-3-azatricyclo<4.3.1.02,7>dec-3-ene-8,9-dicarboxylate (129814-77-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / CH₂Cl₂ / 72 h / 37 °C

2: 78 percent / acetone / 1 h / 0 °C / Irradiation

3: 72 percent / CF₃COOH / CH₂Cl₂ / 24 h / 20 °C

4: Et₃N / CH₂Cl₂ / 24 h / 20 °C

5: 94 percent / 70percent aq.HClO₄, CF₃CH(OH)CF₃ / 1 h / 20 °C

With perchloric acid; C₄H₅F₅O; triethylamine; trifluoroacetic acid; In dichloromethane; acetone;

DOI:10.1002/hlca.19900730316

upstream raw materials:

dimethyl (1RS,2SR,4RS,5SR,6SR,7RS)-3-benzoyl-8-oxa-3-azatricyclo<3.2.1.0^2,4>octane-6,7-dicarboxylate

acetic acid

dimethyl 7-oxabicyclo[2.2.1]hept-5-ene exo,exo-2,3-dicarboxylate

dimethyl (1RS,2SR,4RS,5SR,6SR,7RS)-8-oxa-3-azatricyclo<3.2.1.0^2,4>octane-6,7-dicarboxylate

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