Technology Process of (1S,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-2,12-dioxo-13-azatetracyclo<9.7.0.03,8.011,15>octadec-16-ene 6,7-acetonide
There total 17 articles about (1S,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-2,12-dioxo-13-azatetracyclo<9.7.0.03,8.011,15>octadec-16-ene 6,7-acetonide 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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82770-13-6
(1S,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-2,12-dioxo-13-azatetracyclo<9.7.0.03,8.011,15>octadec-16-ene 6,7-acetonide
- Guidance literature:
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Multi-step reaction with 10 steps
1: 1.) KDA / 1.) THF, 40 min, 2.) -25 deg C, 30 min
2: 1.) potassium tert-butoxide, 2.) ammoniua, lithium / 1.) tert-butyl alcohol, THF, 0 deg C, 5 min, 2.) -78 deg C, 1.5 h
4: 1.) 80percent m-chloroperbenzoic acid, sodium bicarbonate / 1.) methylene chloride, 0 deg C, 25 min, 2.) pyridine, 25 deg C, 3 h
5: 94 percent / methanesulfonic acid, trifluoroacetic acid / CH2Cl2 / 2 h / 25 °C
6: 78 percent / 1 h / 25 °C
7: 67 percent / toluene / 36 h / 110 °C
8: 96 percent / potassium tert-butoxide / H2O; diethyl ether / 20 h / 25 °C
9: 85 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 4 h / 25 °C
10: 1.) L-Selectride, 2.) 5percent aq. sodium hydroxide, 30percent hydrogen peroxide / 1.) THF, -78 deg C, 1 h, 2.) 0 deg C, 10 min
With
sodium hydroxide; methanesulfonic acid; Diethoxy-methyl-(6-amino-hexylaminomethyl)-silan; potassium tert-butylate; ammonia; dihydrogen peroxide; sodium acetate; lithium; L-Selectride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; trifluoroacetic acid;
In
diethyl ether; dichloromethane; water; toluene;
DOI:10.1021/ja00385a030
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82770-13-6
(1S,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-2,12-dioxo-13-azatetracyclo<9.7.0.03,8.011,15>octadec-16-ene 6,7-acetonide
- Guidance literature:
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Multi-step reaction with 12 steps
1: 15.0 g / m-chloroperbenzoic acid / CH2Cl2 / 1.) -35 deg C, 10 min, 2.) -35 deg C -> 25 deg C, 1 h
2: 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / Heating
3: 1.) KDA / 1.) THF, 40 min, 2.) -25 deg C, 30 min
4: 1.) potassium tert-butoxide, 2.) ammoniua, lithium / 1.) tert-butyl alcohol, THF, 0 deg C, 5 min, 2.) -78 deg C, 1.5 h
6: 1.) 80percent m-chloroperbenzoic acid, sodium bicarbonate / 1.) methylene chloride, 0 deg C, 25 min, 2.) pyridine, 25 deg C, 3 h
7: 94 percent / methanesulfonic acid, trifluoroacetic acid / CH2Cl2 / 2 h / 25 °C
8: 78 percent / 1 h / 25 °C
9: 67 percent / toluene / 36 h / 110 °C
10: 96 percent / potassium tert-butoxide / H2O; diethyl ether / 20 h / 25 °C
11: 85 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 4 h / 25 °C
12: 1.) L-Selectride, 2.) 5percent aq. sodium hydroxide, 30percent hydrogen peroxide / 1.) THF, -78 deg C, 1 h, 2.) 0 deg C, 10 min
With
sodium hydroxide; methanesulfonic acid; Diethoxy-methyl-(6-amino-hexylaminomethyl)-silan; potassium tert-butylate; ammonia; dihydrogen peroxide; sodium acetate; lithium; L-Selectride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; trifluoroacetic acid;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; toluene;
DOI:10.1021/ja00385a030
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82770-13-6
(1S,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-2,12-dioxo-13-azatetracyclo<9.7.0.03,8.011,15>octadec-16-ene 6,7-acetonide
- Guidance literature:
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Multi-step reaction with 7 steps
1: 1.) 80percent m-chloroperbenzoic acid, sodium bicarbonate / 1.) methylene chloride, 0 deg C, 25 min, 2.) pyridine, 25 deg C, 3 h
2: 94 percent / methanesulfonic acid, trifluoroacetic acid / CH2Cl2 / 2 h / 25 °C
3: 78 percent / 1 h / 25 °C
4: 67 percent / toluene / 36 h / 110 °C
5: 96 percent / potassium tert-butoxide / H2O; diethyl ether / 20 h / 25 °C
6: 85 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 4 h / 25 °C
7: 1.) L-Selectride, 2.) 5percent aq. sodium hydroxide, 30percent hydrogen peroxide / 1.) THF, -78 deg C, 1 h, 2.) 0 deg C, 10 min
With
sodium hydroxide; methanesulfonic acid; potassium tert-butylate; dihydrogen peroxide; sodium acetate; L-Selectride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; trifluoroacetic acid;
In
diethyl ether; dichloromethane; water; toluene;
DOI:10.1021/ja00385a030
