(1α,2β,3α,6α,7β,8α)-11-benzyloxycarbonyl-11-aza-12-oxatetracyclo[6.2.1.1^3,6.0^2,7]dodeca-4,9-diene-2,7-dicarboxylic anhydride

Base Information

• Chemical Name: (1α,2β,3α,6α,7β,8α)-11-benzyloxycarbonyl-11-aza-12-oxatetracyclo[6.2.1.1^3,6.0^2,7]dodeca-4,9-diene-2,7-dicarboxylic anhydride
• CAS No.: 936640-62-9
• Molecular Formula: C₂₀H₁₅NO₆
• Molecular Weight: 365.342

Synonyms:(1α,2β,3α,6α,7β,8α)-11-benzyloxycarbonyl-11-aza-12-oxatetracyclo[6.2.1.1^3,6.0^2,7]dodeca-4,9-diene-2,7-dicarboxylic anhydride

Chemical Property of (1α,2β,3α,6α,7β,8α)-11-benzyloxycarbonyl-11-aza-12-oxatetracyclo[6.2.1.1^3,6.0^2,7]dodeca-4,9-diene-2,7-dicarboxylic anhydride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1α,2β,3α,6α,7β,8α)-11-benzyloxycarbonyl-11-aza-12-oxatetracyclo[6.2.1.1^3,6.0^2,7]dodeca-4,9-diene-2,7-dicarboxylic anhydride

There total 2 articles about (1α,2β,3α,6α,7β,8α)-11-benzyloxycarbonyl-11-aza-12-oxatetracyclo[6.2.1.1^3,6.0^2,7]dodeca-4,9-diene-2,7-dicarboxylic anhydride 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:

exo,exo-11,12-dioxatetracyclo[6.2.1.13,6.02,7]dodeca-4,9-diene 2,7-dicarboxylic acid (10243-56-8,59823-51-7) → (1α,2β,3α,6α,7β,8α)-11-benzyloxycarbonyl-11-aza-12-oxatetracyclo[6.2.1.13,6.02,7]dodeca-4,9-diene-2,7-dicarboxylic anhydride (936640-62-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / triethyl amine; acetic anhydride / 60 °C

2: 360 °C / 0 Torr / Pyrolysis

3: 30 mg / CDCl₃ / 0.08 h / 20 °C

With acetic anhydride; triethylamine; In chloroform-d1; 2: retro Diels-Alder reaction;

DOI:10.1016/j.tet.2007.03.009

Reference yield:

7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid anhydride + benzyl 1H-pyrrole-1-carboxylate (56857-08-0) → (1α,2β,3α,6α,7β,8α)-11-benzyloxycarbonyl-11-aza-12-oxatetracyclo[6.2.1.13,6.02,7]dodeca-4,9-diene-2,7-dicarboxylic anhydride (936640-62-9)

Guidance literature:

In chloroform-d1; at 20 ℃; for 0.0833333h;

DOI:10.1016/j.tet.2007.03.009

Reference yield:

(1α,2β,3α,6α,7β,8α)-11-benzyloxycarbonyl-11-aza-12-oxatetracyclo[6.2.1.13,6.02,7]dodeca-4,9-diene-2,7-dicarboxylic anhydride (936640-62-9) → 1,3-dioxo-1H,3H-furo[3,4-c]pyrrole-5-carboxylic acid benzyl ester + acetylene (74-86-2,25067-58-7)

Guidance literature:

under 0.00375 Torr; Pyrolysis;

DOI:10.1016/j.tet.2007.03.009

upstream raw materials:

benzyl 1H-pyrrole-1-carboxylate

exo,exo-11,12-dioxatetracyclo[6.2.1.1^3,6.0^2,7]dodeca-4,9-diene 2,7-dicarboxylic acid

Downstream raw materials:

acetylene

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