Technology Process of 7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[bis(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline
There total 19 articles about 7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[bis(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline 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:
- Guidance literature:
-
With
dmap;
In
tetrahydrofuran;
for 2h;
Heating;
DOI:10.1021/ja962431g
- Guidance literature:
-
Multi-step reaction with 14 steps
1.1: 94 percent
2.1: 100 percent / NBS
3.1: 95 percent
4.1: 100 percent / Al-Hg
5.1: 96 percent
6.1: 84 percent / Pb(OAc)4 / 4 h / 25 °C
7.1: BF3*Et2O / CH2Cl2 / 0.5 h / -20 °C
7.2: 89 percent / CH2Cl2 / 3 h / -20 °C
8.1: 95 percent / N-methylmorpholine N-oxide / OsO4 / acetone; H2O; toluene / 25 °C
9.1: Bu2SnO / toluene; tetrahydrofuran / 6 h / Heating
9.2: 94 percent / Et3N / toluene / 12 h / 25 °C
10.1: 75 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C
11.1: 97 percent / NaH / tetrahydrofuran / 2 h / 0 °C
12.1: 45 percent / NH2NH2 / ethanol / 20 h / 140 °C
13.1: 2,6-lutidine / CH2Cl2
13.2: water; citric acid
14.1: 95 percent / DMAP / tetrahydrofuran / 2 h / Heating
With
2,6-dimethylpyridine; lead(IV) acetate; dmap; N-Bromosuccinimide; aluminium amalgam; boron trifluoride diethyl etherate; sodium hydride; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; hydrazine;
osmium(VIII) oxide;
In
tetrahydrofuran; ethanol; dichloromethane; water; acetone; toluene;
1.1: Alkylation / 2.1: Bromination / 3.1: Substitution / 4.1: Reduction / 5.1: Acylation / 6.1: Oxidation / 7.1: Addition / 7.2: Addition / 8.1: hydroxylation / 9.1: Addition / 9.2: Tosylation / 10.1: silylation / 11.1: Cyclization / 12.1: deprotection / 13.1: silylation / 13.2: Hydrolysis / 14.1: protection;
DOI:10.1021/ja962431g
- Guidance literature:
-
Multi-step reaction with 13 steps
1.1: 100 percent / NBS
2.1: 95 percent
3.1: 100 percent / Al-Hg
4.1: 96 percent
5.1: 84 percent / Pb(OAc)4 / 4 h / 25 °C
6.1: BF3*Et2O / CH2Cl2 / 0.5 h / -20 °C
6.2: 89 percent / CH2Cl2 / 3 h / -20 °C
7.1: 95 percent / N-methylmorpholine N-oxide / OsO4 / acetone; H2O; toluene / 25 °C
8.1: Bu2SnO / toluene; tetrahydrofuran / 6 h / Heating
8.2: 94 percent / Et3N / toluene / 12 h / 25 °C
9.1: 75 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C
10.1: 97 percent / NaH / tetrahydrofuran / 2 h / 0 °C
11.1: 45 percent / NH2NH2 / ethanol / 20 h / 140 °C
12.1: 2,6-lutidine / CH2Cl2
12.2: water; citric acid
13.1: 95 percent / DMAP / tetrahydrofuran / 2 h / Heating
With
2,6-dimethylpyridine; lead(IV) acetate; dmap; N-Bromosuccinimide; aluminium amalgam; boron trifluoride diethyl etherate; sodium hydride; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; hydrazine;
osmium(VIII) oxide;
In
tetrahydrofuran; ethanol; dichloromethane; water; acetone; toluene;
1.1: Bromination / 2.1: Substitution / 3.1: Reduction / 4.1: Acylation / 5.1: Oxidation / 6.1: Addition / 6.2: Addition / 7.1: hydroxylation / 8.1: Addition / 8.2: Tosylation / 9.1: silylation / 10.1: Cyclization / 11.1: deprotection / 12.1: silylation / 12.2: Hydrolysis / 13.1: protection;
DOI:10.1021/ja962431g
