Technology Process of (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
There total 13 articles about (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 which
guide to synthetic route it.
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synthetic route:
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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
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219646-86-3
(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
- Guidance literature:
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With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
at 0 ℃;
for 2h;
DOI:10.1002/1521-3765(20010105)7:1<41::AID-CHEM41>3.0.CO;2-D
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219646-86-3
(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
- Guidance literature:
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Multi-step reaction with 7 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
7.1: 96 percent / TBAF / tetrahydrofuran / 2 h / 0 °C
With
pyridine; 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; 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
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219646-86-3
(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
- Guidance literature:
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Multi-step reaction with 4 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
4.1: 96 percent / TBAF / tetrahydrofuran / 2 h / 0 °C
With
2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; 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