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

Base Information

• Chemical Name: 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
• CAS No.: 219646-85-2
• Molecular Formula: C₃₇H₄₅IN₂O₇Si
• Molecular Weight: 784.764

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 11 articles about 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 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: 90.0%

3a-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1,8-dibenzyl ester 2-tert-butyl ester (219646-82-9) → 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 (219646-85-2)

Guidance literature:

With 2,6-di-tert-butyl-pyridine; Iodine monochloride; In dichloromethane;

DOI:10.1002/(SICI)1521-3773(19981116)37:21<2993::AID-ANIE2993>3.0.CO;2-I

Reference yield:

Nb-Anthracene-9-sulfonyltryptophan tert-butyl ester (219646-69-2) → 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 (219646-85-2)

Guidance literature:

Multi-step reaction with 7 steps

1: NBS; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 3,3-dimethyldioxirane / acetone; CH₂Cl₂ / 0.17 h / -78 °C

3: 8.00 g / NaBH₄ / methanol; acetone; CH₂Cl₂ / 4 h / 0 - 20 °C

4: Al(Hg); aq. NH₄OAc / tetrahydrofuran / 2 h / 0 °C

5: 3.82 g / pyridine / CH₂Cl₂ / 0 - 20 °C

6: 77 percent / DBU / dimethylformamide / 5 h / 50 °C

7: 81 percent / ICl; 2,6-di-tert-butylpyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

With pyridine; sodium tetrahydroborate; aluminum amalgam; N-Bromosuccinimide; 2,6-di-tert-butyl-pyridine; ammonium acetate; 3,3-dimethyldioxirane; Iodine monochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

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

Reference yield:

1-(anthracene-9-sulfonyl)-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid tert-butyl ester (219646-76-1) → 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 (219646-85-2)

Guidance literature:

Multi-step reaction with 4 steps

1: Al(Hg); aq. NH₄OAc / tetrahydrofuran / 2 h / 0 °C

2: 3.82 g / pyridine / CH₂Cl₂ / 0 - 20 °C

3: 77 percent / DBU / dimethylformamide / 5 h / 50 °C

4: 81 percent / ICl; 2,6-di-tert-butylpyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

With pyridine; aluminum amalgam; 2,6-di-tert-butyl-pyridine; ammonium acetate; Iodine monochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

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

upstream raw materials:

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

benzyl chloroformate

N_b-Anthracene-9-sulfonyltryptophan tert-butyl ester

1-(anthracene-9-sulfonyl)-1,2,3,8-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid tert-butyl ester

Downstream raw materials:

(2R,3aR,8aR,2'R,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

(2R,3aR,8aR,2'R,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

(2R,3aR,8aR,2'R,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

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