3a-hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

• Chemical Name: 3a-hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
• CAS No.: 643751-48-8
• Molecular Formula: C₂₀H₂₀N₂O₅
• Molecular Weight: 368.389

Synonyms:3a-hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property of 3a-hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 3a-hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 5 articles about 3a-hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 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: 97.0%

3a-hydroxy-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1-benzyl ester 8-tert-butyl ester 2-methyl ester (643751-46-6) → 3a-hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (643751-48-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.0833333h;

DOI:10.1039/b308288a

Reference yield:

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester (2717-76-2,130812-44-1,130812-46-3) → 3a-hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (643751-48-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / NaOH; Bu₄NHSO₄ / CH₂Cl₂

2: 93 percent / PPTS; Na₂SO₄ / CH₂Cl₂

3: 100 percent / mCPBA; K₂CO₃ / CH₂Cl₂ / 0 - 25 °C

4: 97 percent / TFA / CH₂Cl₂ / 0.08 h

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; potassium carbonate; sodium sulfate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane;

DOI:10.1039/b308288a

Reference yield:

N-carbobenzyloxy-1-tert-butoxycarbonyl-L-tryptophan methyl ester (643751-42-2) → 3a-hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (643751-48-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / PPTS; Na₂SO₄ / CH₂Cl₂

2: 100 percent / mCPBA; K₂CO₃ / CH₂Cl₂ / 0 - 25 °C

3: 97 percent / TFA / CH₂Cl₂ / 0.08 h

With pyridinium p-toluenesulfonate; potassium carbonate; sodium sulfate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane;

DOI:10.1039/b308288a

upstream raw materials:

3a-hydroxy-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1-benzyl ester 8-tert-butyl ester 2-methyl ester

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester

N-carbobenzyloxy-1-tert-butoxycarbonyl-L-tryptophan methyl ester

3a-phenylselanyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1-benzyl ester 8-tert-butyl ester 2-methyl ester

Downstream raw materials:

(2S,3aR,8aS)-1-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionyl]-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

(2S,3aR,8aS)-1-((2S,3R)-3-Benzyloxy-2-benzyloxycarbonylamino-butyryl)-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

(2S,3aR,8aS)-1-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

(2S,3aR,8aS)-1-((S)-1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

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