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

Base Information

• Chemical Name: trans-(1S,3R)-(+)-methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-6-oxocanthine-2-carboxylate
• CAS No.: 84129-58-8
• Molecular Formula: C₂₃H₂₂N₂O₃
• Molecular Weight: 374.439

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

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

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

There total 10 articles about trans-(1S,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: 88.0%

(1S,3R)-(-)-methyl 2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate (84094-74-6) → trans-(1S,3R)-(+)-methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-6-oxocanthine-2-carboxylate (84129-58-8)

Guidance literature:

With sodium hydride; In methanol; toluene; for 0.166667h; Heating;

DOI:10.1021/jo000126e

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

upstream raw materials:

α-ketoglutaric acid

D-(+)-N_bbenzyltryptophan methyl ester

(1S,3R)-(-)-2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid

(1S,3R)-(-)-methyl 2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate

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