methyl (1RS,2RS,3SR,6RS,7SR,9RS)-2-(benzoylamino)-5-oxo-4,8-dioxatricyclo<4.2.1.0^3,7>nonane-9-carboxylate

Base Information

• Chemical Name: methyl (1RS,2RS,3SR,6RS,7SR,9RS)-2-(benzoylamino)-5-oxo-4,8-dioxatricyclo<4.2.1.0^3,7>nonane-9-carboxylate
• CAS No.: 129814-60-4
• Molecular Formula: C₁₆H₁₅NO₆
• Molecular Weight: 317.298

Synonyms:methyl (1RS,2RS,3SR,6RS,7SR,9RS)-2-(benzoylamino)-5-oxo-4,8-dioxatricyclo<4.2.1.0^3,7>nonane-9-carboxylate

Chemical Property of methyl (1RS,2RS,3SR,6RS,7SR,9RS)-2-(benzoylamino)-5-oxo-4,8-dioxatricyclo<4.2.1.0^3,7>nonane-9-carboxylate

Chemical Property:

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Technology Process of methyl (1RS,2RS,3SR,6RS,7SR,9RS)-2-(benzoylamino)-5-oxo-4,8-dioxatricyclo<4.2.1.0^3,7>nonane-9-carboxylate

There total 6 articles about methyl (1RS,2RS,3SR,6RS,7SR,9RS)-2-(benzoylamino)-5-oxo-4,8-dioxatricyclo<4.2.1.0^3,7>nonane-9-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: 65.0%

dimethyl (1RS,2SR,4RS,5SR,6RS,7RS)-3-benzoyl-8-oxa-3-azatricyclo<3.2.1.02,4>octane-6,7-dicarboxylate (129814-71-7,129893-72-7) → methyl (1RS,2RS,3SR,6RS,7SR,9RS)-2-(benzoylamino)-5-oxo-4,8-dioxatricyclo<4.2.1.03,7>nonane-9-carboxylate (129814-60-4)

Guidance literature:

With hydrogen bromide; In dichloromethane; acetic acid; 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) → methyl (1RS,2RS,3SR,6RS,7SR,9RS)-2-(benzoylamino)-5-oxo-4,8-dioxatricyclo<4.2.1.03,7>nonane-9-carboxylate (129814-60-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / aq.NaHCO₃ / CH₂Cl₂ / 48 h / 37 °C

2: K₂CO₃ / CH₂Cl₂ / 2 h / 20 °C

3: 99 percent / acetone / 3 h / 0 °C / Irradiation

4: 76 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

5: 65 percent / HBr / aq. acetic acid; CH₂Cl₂ / 24 h / 20 °C

With pyridine; hydrogen bromide; sodium hydrogencarbonate; potassium carbonate; In dichloromethane; acetic acid; acetone;

DOI:10.1002/hlca.19900730316

Reference yield:

3-ethyl 8,9-dimethyl (1RS,2SR,6RS,7SR,8SR,9RS)-10-oxa-3,4,5-triazatricyclo<5.2.1.02,6>dec-4-ene-3,8,9-tricarboxylate (129814-78-4) → methyl (1RS,2RS,3SR,6RS,7SR,9RS)-2-(benzoylamino)-5-oxo-4,8-dioxatricyclo<4.2.1.03,7>nonane-9-carboxylate (129814-60-4)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂CO₃ / CH₂Cl₂ / 2 h / 20 °C

2: 99 percent / acetone / 3 h / 0 °C / Irradiation

3: 76 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

4: 65 percent / HBr / aq. acetic acid; CH₂Cl₂ / 24 h / 20 °C

With pyridine; hydrogen bromide; potassium carbonate; In dichloromethane; acetic acid; acetone;

DOI:10.1002/hlca.19900730316

upstream raw materials:

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

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

3-ethyl 8,9-dimethyl (1RS,2SR,6RS,7SR,8SR,9RS)-10-oxa-3,4,5-triazatricyclo<5.2.1.0^2,6>dec-4-ene-3,8,9-tricarboxylate

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

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