(1R)-N-Benzyl-7-oxo-6-hydroxy-1beta,2beta,3,6-tetrahydro-3beta,6beta-(epoxymethano)phthalimide

Base Information

• Chemical Name: (1R)-N-Benzyl-7-oxo-6-hydroxy-1beta,2beta,3,6-tetrahydro-3beta,6beta-(epoxymethano)phthalimide
• CAS No.: 289041-19-6
• Molecular Formula: C₁₆H₁₃NO₅
• Molecular Weight: 299.283
• DSSTox Substance ID: DTXSID401108190
• Nikkaji Number: J1.331.890E

Synonyms:DTXSID401108190;(1R)-N-Benzyl-7-oxo-6-hydroxy-1beta,2beta,3,6-tetrahydro-3beta,6beta-(epoxymethano)phthalimide;(3aS,4S,7S,7aR)-3a,4,7,7a-Tetrahydro-7-hydroxy-2-(phenylmethyl)-4,7-ethenopyrano[3,4-c]pyrrole-1,3,6(2H)-trione;289041-19-6

Chemical Property of (1R)-N-Benzyl-7-oxo-6-hydroxy-1beta,2beta,3,6-tetrahydro-3beta,6beta-(epoxymethano)phthalimide

Chemical Property:

• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 299.07937252
• Heavy Atom Count: 22
• Complexity: 579

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CN2C(=O)C3C4C=CC(C3C2=O)(C(=O)O4)O
• Isomeric SMILES: C1=CC=C(C=C1)CN2C(=O)[C@@H]3[C@@H]4C=C[C@]([C@@H]3C2=O)(C(=O)O4)O

Technology Process of (1R)-N-Benzyl-7-oxo-6-hydroxy-1beta,2beta,3,6-tetrahydro-3beta,6beta-(epoxymethano)phthalimide

There total 3 articles about (1R)-N-Benzyl-7-oxo-6-hydroxy-1beta,2beta,3,6-tetrahydro-3beta,6beta-(epoxymethano)phthalimide 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: 98.0%

3-hydroxy-2-pyrone (496-64-0) + 1-benzyl-1H-pyrrole-2,5-dione (1631-26-1) → (3aS,4S,7S,7aR)-4,7-ethenopyranol[3,4-c]pyrrole-1,3,6(2H)-trione-3a,4,7,7a-tetrahydro-7-hydroxy-2-(phenylmethyl) (289041-19-6)

Guidance literature:

With C₅₉H₅₀CuN₄O₅S; In tetrahydrofuran; at -40 ℃; Reagent/catalyst; Temperature; enantioselective reaction; Catalytic behavior; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.202009093

Reference yield:

3-hydroxy-2-pyrone (496-64-0) + 1-benzyl-1H-pyrrole-2,5-dione (1631-26-1) → (1R,2S,6R,7R)-4-Benzyl-1-hydroxy-8-oxa-4-aza-tricyclo[5.2.2.02,6]undec-10-ene-3,5,9-trione + (3aS,4S,7S,7aR)-4,7-ethenopyranol[3,4-c]pyrrole-1,3,6(2H)-trione-3a,4,7,7a-tetrahydro-7-hydroxy-2-(phenylmethyl) (289041-19-6)

Guidance literature:

With Quinine; In dichloromethane; at -78 - -20 ℃; for 12h;

DOI:10.1016/S0040-4039(00)00555-4

Reference yield:

3-hydroxy-2-pyrone (496-64-0) + 1-benzyl-1H-pyrrole-2,5-dione (1631-26-1) → C16H13NO5 + (3aS,4S,7S,7aR)-4,7-ethenopyranol[3,4-c]pyrrole-1,3,6(2H)-trione-3a,4,7,7a-tetrahydro-7-hydroxy-2-(phenylmethyl) (289041-19-6)

Guidance literature:

With C₂₁H₁₄O₃; caesium carbonate; In tetrahydrofuran; at -40 ℃; for 22h; Inert atmosphere;

DOI:10.1002/anie.202009093

upstream raw materials:

3-hydroxy-2-pyrone

1-benzyl-1H-pyrrole-2,5-dione

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