Technology Process of (5S,8S,11R,14S,17R,20S,22aS)-5,11-Dibenzyl-8,14-bis-(tert-butyl-dimethyl-silanyloxymethyl)-20-((S)-1-hydroxy-ethyl)-17-isopropyl-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone
There total 25 articles about (5S,8S,11R,14S,17R,20S,22aS)-5,11-Dibenzyl-8,14-bis-(tert-butyl-dimethyl-silanyloxymethyl)-20-((S)-1-hydroxy-ethyl)-17-isopropyl-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone 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:
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184296-07-9
(5S,8S,11R,14S,17R,20S,22aS)-5,11-Dibenzyl-8,14-bis-(tert-butyl-dimethyl-silanyloxymethyl)-20-((S)-1-hydroxy-ethyl)-17-isopropyl-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone
- Guidance literature:
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With
pentafluorophenyl diphenyl-phosphinate; sodium hydrogencarbonate;
In
N,N-dimethyl-formamide;
at 40 ℃;
for 72h;
DOI:10.1021/ja962859f
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184296-07-9
(5S,8S,11R,14S,17R,20S,22aS)-5,11-Dibenzyl-8,14-bis-(tert-butyl-dimethyl-silanyloxymethyl)-20-((S)-1-hydroxy-ethyl)-17-isopropyl-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone
- Guidance literature:
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Multi-step reaction with 13 steps
1: N-methylmorpholine / CH2Cl2 / 0.25 h / -15 °C
2: CH2Cl2 / 0 - 20 °C
3: imidazole / CH2Cl2
4: H2 / Pd/C / methanol
5: CH2Cl2 / 0 - 20 °C
6: imidazole / CH2Cl2
7: H2 / Pd/C / methanol / 2 h
8: CH2Cl2 / 1 h / 0 - 20 °C
9: 95 percent / aq. LiOH / tetrahydrofuran / 3 h / Ambient temperature
10: Et3N, pentafluorophenyl diphenylphosphinate / CH2Cl2 / Ambient temperature
11: 92 percent / H2 / Pd/C / methanol / 24 h
12: aq. NaOH / tetrahydrofuran; methanol / 4 h / Ambient temperature
13: 48 percent / NaHCO3, pentafluorophenyl diphenylphosphinate / dimethylformamide / 72 h / 40 °C
With
4-methyl-morpholine; 1H-imidazole; lithium hydroxide; sodium hydroxide; pentafluorophenyl diphenyl-phosphinate; hydrogen; sodium hydrogencarbonate; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja962859f
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184296-07-9
(5S,8S,11R,14S,17R,20S,22aS)-5,11-Dibenzyl-8,14-bis-(tert-butyl-dimethyl-silanyloxymethyl)-20-((S)-1-hydroxy-ethyl)-17-isopropyl-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone
- Guidance literature:
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Multi-step reaction with 11 steps
1: imidazole / CH2Cl2
2: H2 / Pd/C / methanol
3: CH2Cl2 / 0 - 20 °C
4: imidazole / CH2Cl2
5: H2 / Pd/C / methanol / 2 h
6: CH2Cl2 / 1 h / 0 - 20 °C
7: 95 percent / aq. LiOH / tetrahydrofuran / 3 h / Ambient temperature
8: Et3N, pentafluorophenyl diphenylphosphinate / CH2Cl2 / Ambient temperature
9: 92 percent / H2 / Pd/C / methanol / 24 h
10: aq. NaOH / tetrahydrofuran; methanol / 4 h / Ambient temperature
11: 48 percent / NaHCO3, pentafluorophenyl diphenylphosphinate / dimethylformamide / 72 h / 40 °C
With
1H-imidazole; lithium hydroxide; sodium hydroxide; pentafluorophenyl diphenyl-phosphinate; hydrogen; sodium hydrogencarbonate; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja962859f