Technology Process of (2S,5S,11S,14R,17(R,S),18S)-N-<11-<4-(tert-butyloxy)benzyl>-14-benzyl-17-hydroxy-18-<<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>propyl>-4,8,13,16,17,20-hexaoxo-2,3,4,5,6,7,8,11,12,13,14,15,16,17,18,19,20,20a-octadeca...
There total 23 articles about (2S,5S,11S,14R,17(R,S),18S)-N-<11-<4-(tert-butyloxy)benzyl>-14-benzyl-17-hydroxy-18-<<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>propyl>-4,8,13,16,17,20-hexaoxo-2,3,4,5,6,7,8,11,12,13,14,15,16,17,18,19,20,20a-octadeca... 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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190385-10-5
(2S,5S,11S,14R,17(R,S),18S)-N-<11-<4-(tert-butyloxy)benzyl>-14-benzyl-17-hydroxy-18-<<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>propyl>-4,8,13,16,20-pentaoxo-2,3,4,5,6,7,8,11,12,13,14,15,16,17,18,19,20,20a-octadeca...
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190203-31-7
(2S,5S,11S,14R,17(R,S),18S)-N-<11-<4-(tert-butyloxy)benzyl>-14-benzyl-17-hydroxy-18-<<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>propyl>-4,8,13,16,17,20-hexaoxo-2,3,4,5,6,7,8,11,12,13,14,15,16,17,18,19,20,20a-octadeca...
- Guidance literature:
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With
Dess-Martin periodane; tert-butyl alcohol;
In
dichloromethane; acetonitrile;
at 40 ℃;
for 24h;
DOI:10.1021/jo961447m
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190203-31-7
(2S,5S,11S,14R,17(R,S),18S)-N-<11-<4-(tert-butyloxy)benzyl>-14-benzyl-17-hydroxy-18-<<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>propyl>-4,8,13,16,17,20-hexaoxo-2,3,4,5,6,7,8,11,12,13,14,15,16,17,18,19,20,20a-octadeca...
- Guidance literature:
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Multi-step reaction with 14 steps
1: 1.) CuCO3, 2.) DIPEA, 3.) EDTA, NaHCO3 / 1.) H2O, 100 deg C, 1 h, 2.) formamide, room temperature, 24 h, 3.) acetone, H2O, room temperature, 12 h
2: 91 percent / CH2Cl2; ethanol / 0 °C
3: 97 percent / DIBALH / CH2Cl2; hexane / 1.25 h / -65 °C
4: 53.6 percent / n-BuLi / hexane; tetrahydrofuran / 5 h / -65 °C / 1.) 20 min, 2.) 5 h
5: 79 percent / HgCl2, HgO / H2O / 72 h / Ambient temperature
6: 96.4 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 0.2 h / Ambient temperature
7: 61.3 percent / HOBt, DCC, DIPEA / CH2Cl2 / 1.) 0 deg C, 45 min, 2.) 0 deg C, 30 min; 18 h
8: 100 percent / H2 / Pd-C / methanol / 6 h
9: 79.1 percent / DIPEA, TBTU / CH2Cl2 / 2.5 h
10: 99.7 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 0.2 h
11: 85.3 percent / DIPEA, TBTU / CH2Cl2 / 3 h / Ambient temperature
12: 1.) Pd(PPh3)4, morpholine, 2.) SiO2 / 1.) THF, room temperature, 45 min, 2.) CH2Cl2, MeOH
13: 60.6 percent / TBTU, HOBt, DMAP / CH2Cl2 / 23 h / Ambient temperature
14: 89 percent / Dess-Martin periodinane, t-BuOH / CH2Cl2; acetonitrile / 24 h / 40 °C
With
morpholine; dmap; copper(II) carbonate; lithium hydroxide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; ethylenediaminetetraacetic acid; hydrogen; silica gel; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; Dess-Martin periodane; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; mercury dichloride; mercury(II) oxide; tert-butyl alcohol;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetonitrile;
DOI:10.1021/jo961447m
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190203-31-7
(2S,5S,11S,14R,17(R,S),18S)-N-<11-<4-(tert-butyloxy)benzyl>-14-benzyl-17-hydroxy-18-<<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>propyl>-4,8,13,16,17,20-hexaoxo-2,3,4,5,6,7,8,11,12,13,14,15,16,17,18,19,20,20a-octadeca...
- Guidance literature:
-
Multi-step reaction with 14 steps
1: 1.) CuCO3, 2.) DIPEA, 3.) EDTA, NaHCO3 / 1.) H2O, 100 deg C, 1 h, 2.) formamide, room temperature, 24 h, 3.) acetone, H2O, room temperature, 12 h
2: 91 percent / CH2Cl2; ethanol / 0 °C
3: 97 percent / DIBALH / CH2Cl2; hexane / 1.25 h / -65 °C
4: 53.6 percent / n-BuLi / hexane; tetrahydrofuran / 5 h / -65 °C / 1.) 20 min, 2.) 5 h
5: 79 percent / HgCl2, HgO / H2O / 72 h / Ambient temperature
6: 96.4 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 0.2 h / Ambient temperature
7: 61.3 percent / HOBt, DCC, DIPEA / CH2Cl2 / 1.) 0 deg C, 45 min, 2.) 0 deg C, 30 min; 18 h
8: 100 percent / H2 / Pd-C / methanol / 6 h
9: 79.1 percent / DIPEA, TBTU / CH2Cl2 / 2.5 h
10: 99.7 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 0.2 h
11: 85.3 percent / DIPEA, TBTU / CH2Cl2 / 3 h / Ambient temperature
12: 1.) Pd(PPh3)4, morpholine, 2.) SiO2 / 1.) THF, room temperature, 45 min, 2.) CH2Cl2, MeOH
13: 60.6 percent / TBTU, HOBt, DMAP / CH2Cl2 / 23 h / Ambient temperature
14: 89 percent / Dess-Martin periodinane, t-BuOH / CH2Cl2; acetonitrile / 24 h / 40 °C
With
morpholine; dmap; copper(II) carbonate; lithium hydroxide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; ethylenediaminetetraacetic acid; hydrogen; silica gel; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; Dess-Martin periodane; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; mercury dichloride; mercury(II) oxide; tert-butyl alcohol;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetonitrile;
DOI:10.1021/jo961447m
