3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid tert-butyl ester
• CAS No.: 219646-54-5
• Molecular Formula: C₃₄H₃₄N₂O₃
• Molecular Weight: 518.656

Synonyms:3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid tert-butyl ester

Chemical Property of 3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid tert-butyl ester

There total 4 articles about 3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid tert-butyl 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:

Nb-trityl-L-tryptophan tert-butyl ester (219646-53-4) → 3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid tert-butyl ester (219646-54-5)

Guidance literature:

With 3,3-dimethyldioxirane; In dichloromethane; acetone; at -78 ℃; for 0.5h;

DOI:10.1002/1521-3765(20010105)7:1<41::AID-CHEM41>3.0.CO;2-D

Reference yield:

trityl chloride (76-83-5) → 3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid tert-butyl ester (219646-54-5)

Guidance literature:

Multi-step reaction with 3 steps

1: ET₃N / tetrahydrofuran

2: 34.0 g / CH₂Cl₂ / 36 h / 0 - 20 °C

3: 3,3-dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h / -78 °C

With 3,3-dimethyldioxirane; triethylamine; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1002/1521-3765(20010105)7:1<41::AID-CHEM41>3.0.CO;2-D

Reference yield:

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → 3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid tert-butyl ester (219646-54-5)

Guidance literature:

Multi-step reaction with 3 steps

1: ET₃N / tetrahydrofuran

2: 34.0 g / CH₂Cl₂ / 36 h / 0 - 20 °C

3: 3,3-dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h / -78 °C

With 3,3-dimethyldioxirane; triethylamine; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1002/1521-3765(20010105)7:1<41::AID-CHEM41>3.0.CO;2-D

upstream raw materials:

N_b-trityl-L-tryptophan tert-butyl ester

trityl chloride

L-Tryptophan

(S)-3-(1H-indol-3-yl)-2-(tritylamino)propanoic acid

Downstream raw materials:

(2S,3aR,8aR,2'S,3'aR,8'aR)-3a,3'a-Bis-triethylsilanyloxy-2,3,3a,8a,2',3',3'a,8'a-octahydro-[5,5']bi[pyrrolo[2,3-b]indolyl]-1,2,8,1',2',8'-hexacarboxylic acid 1,8,1',8'-tetrabenzyl ester 2,2'-di-tert-butyl ester

(2S,3aR,8aR,2'S,3'aR,8'aR)-3a,3'a-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,8a,2',3',3'a,8'a-octahydro-[5,5']bi[pyrrolo[2,3-b]indolyl]-1,2,8,1',2',8'-hexacarboxylic acid 1,8,1',8'-tetrabenzyl ester 2,2'-di-tert-butyl ester

(2S,3aR,8aR,2'S,3'aR,8'aR)-3a,3'a-Dihydroxy-2,3,3a,8a,2',3',3'a,8'a-octahydro-[5,5']bi[pyrrolo[2,3-b]indolyl]-1,2,8,1',2',8'-hexacarboxylic acid 1,8,1',8'-tetrabenzyl ester 2,2'-di-tert-butyl ester

3a-(tert-butyl-dimethyl-silanyloxy)-5-iodo-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1,8-dibenzyl ester 2-tert-butyl ester

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