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

Base Information

• Chemical Name: 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
• CAS No.: 643751-44-4
• Molecular Formula: C₃₁H₃₂N₂O₆Se
• Molecular Weight: 607.565
• Mol file: 643751-44-4.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 4 articles about 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 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: 93.0%

N-phenylselanylphthalimide (71098-88-9) + N-carbobenzyloxy-1-tert-butoxycarbonyl-L-tryptophan methyl ester (643751-42-2) → 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 (643751-44-4)

Guidance literature:

With pyridinium p-toluenesulfonate; sodium sulfate; In dichloromethane;

DOI:10.1039/b308288a

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 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 (643751-44-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / NaOH; Bu₄NHSO₄ / CH₂Cl₂

2: 93 percent / PPTS; Na₂SO₄ / CH₂Cl₂

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; sodium sulfate; In dichloromethane;

DOI:10.1039/b308288a

Reference yield:

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester (2717-76-2,130812-44-1,130812-46-3) → 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 (643751-44-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / NaOH; Bu₄NHSO₄ / CH₂Cl₂

2: 93 percent / PPTS; Na₂SO₄ / CH₂Cl₂

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; sodium sulfate; In dichloromethane;

DOI:10.1039/b308288a

upstream raw materials:

N-phenylselanylphthalimide

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

di-tert-butyl dicarbonate

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

Downstream raw materials:

(3S,5aS,10bR,11aS)-3-Benzyl-10b-hydroxy-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione

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

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