(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

Base Information

Chemical Name:(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
CAS No.:219646-59-0
Molecular Formula:C₇₄H₉₀N₄O₁₄Si₂
Molecular Weight:1315.72
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 14 articles about (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 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:

: 219646-56-7
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

: 219646-59-0
(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

Guidance literature:: With triphenyl-arsane; hexamethyldistannane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; Yield given; Multistep reaction; 1.) THF, 2.) DMF, 45 deg C;
DOI:10.1002/(SICI)1521-3773(19981116)37:21<2995::AID-ANIE2995>3.0.CO;2-6

Reference yield:

: 219646-53-4
N_b-trityl-L-tryptophan tert-butyl ester

: 219646-59-0
(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

Guidance literature:: Multi-step reaction with 6 steps

1.1: 3,3-dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h / -78 °C

2.1: 3.00 g / AcOH / CH₂Cl₂; methanol / 2 h / 20 °C

3.1: 63 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

4.1: 97 percent / DBU / dimethylformamide / 8 h / 20 °C

5.1: 73 percent / ICl; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

6.1: Me₆Sn₂ / Pd(PPh₃)4 / tetrahydrofuran / 5 h / 60 °C

6.2: 2.77 g / Ph₃As / Pd₂(dba)3 / dimethylformamide / 22 h / 45 °C

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; hexamethyldistannane; 3,3-dimethyldioxirane; Iodine monochloride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; 6.2: Stille coupling reaction;
DOI:10.1002/1521-3765(20010105)7:1<41::AID-CHEM41>3.0.CO;2-D

Reference yield:

: 329786-96-1
3a-hydroxy-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1,8-dibenzyl ester 2-tert-butyl ester

: 219646-59-0
(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

Guidance literature:: Multi-step reaction with 3 steps

1.1: 97 percent / DBU / dimethylformamide / 8 h / 20 °C

2.1: 73 percent / ICl; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

3.1: Me₆Sn₂ / Pd(PPh₃)4 / tetrahydrofuran / 5 h / 60 °C

3.2: 2.77 g / Ph₃As / Pd₂(dba)3 / dimethylformamide / 22 h / 45 °C

With 2,6-di-tert-butyl-4-methylpyridine; hexamethyldistannane; Iodine monochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3.2: Stille coupling reaction;
DOI:10.1002/1521-3765(20010105)7:1<41::AID-CHEM41>3.0.CO;2-D