Technology Process of (5S,8R,10S,14S,15R,18S,19R,22S,24aS)-18-Amino-14-hydroxy-5-isobutyl-10,15-diisopropyl-22-(4-methoxy-benzyl)-8,19,23-trimethyl-tetradecahydro-11,20-dioxa-3a,6,16,23-tetraaza-cyclopentacyclotricosene-4,7,9,12,17,21,24-heptaone
There total 14 articles about (5S,8R,10S,14S,15R,18S,19R,22S,24aS)-18-Amino-14-hydroxy-5-isobutyl-10,15-diisopropyl-22-(4-methoxy-benzyl)-8,19,23-trimethyl-tetradecahydro-11,20-dioxa-3a,6,16,23-tetraaza-cyclopentacyclotricosene-4,7,9,12,17,21,24-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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117733-99-0
(5S,10S,14S,15R,18S,22S,24aS)-18-Amino-14-hydroxy-5-isobutyl-10,15-diisopropyl-22-(4-methoxy-benzyl)-8,19,23-trimethyl-tetradecahydro-11,20-dioxa-3a,6,16,23-tetraaza-cyclopentacyclotricosene-4,7,9,12,17,21,24-heptaone
- Guidance literature:
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With
hydrogen;
palladium on activated charcoal;
In
methanol;
for 2h;
under 760 Torr;
Ambient temperature;
DOI:10.1021/jo00264a022
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117733-99-0
(5S,10S,14S,15R,18S,22S,24aS)-18-Amino-14-hydroxy-5-isobutyl-10,15-diisopropyl-22-(4-methoxy-benzyl)-8,19,23-trimethyl-tetradecahydro-11,20-dioxa-3a,6,16,23-tetraaza-cyclopentacyclotricosene-4,7,9,12,17,21,24-heptaone
- Guidance literature:
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Multi-step reaction with 14 steps
1: 98 percent / triethylamine (TEA) / tetrahydrofuran / 2 h / 0 - 5 °C
2: lithium diisopropylamide / 1.) THF, hexane, from -78 deg C to -70 deg C, 15 min
3: NaBH4 / CH2Cl2; acetic acid / 1 h / 0 - 5 °C
4: p-toluenesulfonic acid / 1.) reflux, 3 h, 2.) room temperature, overnight
5: 98 percent / 2 M NaOH / methanol / 0 - 5 °C
6: 92 percent / triethylamine (TEA), 4-(dimethylamino)pyridine (DMAP), isopropenyl chlorocarbonate (IPCC) / CH2Cl2 / 0.25 h / -5 °C
7: 100 percent / H2 / 10percent Pd/C / propan-2-ol / 760 Torr
8: 97 percent / triethylamine (TEA) / tetrahydrofuran / 2 h / 0 - 5 °C
9: lithium diisopropylamide / 1.) THF, hexane, from -78 deg C to -70 deg C, 15 min
10: triethylamine (TEA), CuI / CH2Cl2 / 0.5 h / Ambient temperature
11: morpholine / tetrakis(triphenylphosphine)palladium / tetrahydrofuran / 0.17 h
12: 0.5 h
13: 54 percent / (1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), NaHCO3 / dimethylformamide / 24 h / Ambient temperature
14: 100 percent / H2 / 10percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature
With
morpholine; dmap; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; Isopropenyl chloroformate; hydrogen; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide;
palladium on activated charcoal; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jo00264a022
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117733-99-0
(5S,10S,14S,15R,18S,22S,24aS)-18-Amino-14-hydroxy-5-isobutyl-10,15-diisopropyl-22-(4-methoxy-benzyl)-8,19,23-trimethyl-tetradecahydro-11,20-dioxa-3a,6,16,23-tetraaza-cyclopentacyclotricosene-4,7,9,12,17,21,24-heptaone
- Guidance literature:
-
Multi-step reaction with 2 steps
1: 54 percent / (1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), NaHCO3 / dimethylformamide / 24 h / Ambient temperature
2: 100 percent / H2 / 10percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature
With
hydrogen; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate;
palladium on activated charcoal;
In
methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo00264a022