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>-4,8,13,16,20-pentaoxo-2,3,4,5,6,7,8,11,12,13,14,15,16,17,18,19,20,20a-octadeca...
There total 22 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>-4,8,13,16,20-pentaoxo-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...
- Guidance literature:
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With
dmap; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate;
In
dichloromethane;
for 18h;
DOI:10.1016/00404-0399(50)11539-
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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...
- Guidance literature:
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Multi-step reaction with 13 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
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; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; mercury dichloride; mercury(II) oxide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water;
DOI:10.1021/jo961447m
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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...
- Guidance literature:
-
Multi-step reaction with 13 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
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; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; mercury dichloride; mercury(II) oxide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water;
DOI:10.1021/jo961447m
