cis-(1R,3R)-(+)-methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-6-oxocanthine-2-carboxylate

Base Information

• Chemical Name: cis-(1R,3R)-(+)-methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-6-oxocanthine-2-carboxylate
• CAS No.: 84129-59-9
• Molecular Formula: C₂₃H₂₂N₂O₃
• Molecular Weight: 374.439

Synonyms:cis-(1R,3R)-(+)-methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-6-oxocanthine-2-carboxylate

Chemical Property of cis-(1R,3R)-(+)-methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-6-oxocanthine-2-carboxylate

Chemical Property:

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Technology Process of cis-(1R,3R)-(+)-methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-6-oxocanthine-2-carboxylate

There total 8 articles about cis-(1R,3R)-(+)-methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-6-oxocanthine-2-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: 70.0%

α-ketoglutaric acid (328-50-7) + D-(+)-Nbbenzyltryptophan methyl ester (63229-68-5,73327-10-3,84094-71-3) → trans-(1S,3R)-(+)-methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-6-oxocanthine-2-carboxylate (84129-58-8) + cis-(1R,3R)-(+)-methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-6-oxocanthine-2-carboxylate (84129-59-9)

Guidance literature:

With toluene-4-sulfonic acid; In 1,4-dioxane; benzene; for 48h; Heating;

DOI:10.1021/jo000126e

Reference yield: 70.0%

trans-(3R)-(-)-2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-1-propionic acid → trans-(1S,3R)-(+)-methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-6-oxocanthine-2-carboxylate (84129-58-8) + cis-(1R,3R)-(+)-methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-6-oxocanthine-2-carboxylate (84129-59-9)

Guidance literature:

With toluene-4-sulfonic acid; In 1,4-dioxane; benzene; for 36h; Heating;

DOI:10.1021/jo000126e

Reference yield: 5.5%

α-ketoglutaric acid (328-50-7) + D-(+)-Nbbenzyltryptophan methyl ester (63229-68-5,73327-10-3,84094-71-3) → (1S,3R)-(-)-2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid (84094-72-4) + (1R,3R)-(-)-2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid (84094-73-5) + trans-(1S,3R)-(+)-methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-6-oxocanthine-2-carboxylate (84129-58-8) + cis-(1R,3R)-(+)-methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-6-oxocanthine-2-carboxylate (84129-59-9)

Guidance literature:

In 1,4-dioxane; benzene; for 8h; Yield given; Heating;

upstream raw materials:

α-ketoglutaric acid

D-(+)-N_bbenzyltryptophan methyl ester

benzaldehyde

D-Tryptophan methyl ester

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