Technology Process of 2-(p-trifluoroacetamidophenyl)ethyl 4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)-2,3-diacetamido-6-O-benzyl-2,3-dideoxy-α-D-mannopyranoside
There total 9 articles about 2-(p-trifluoroacetamidophenyl)ethyl 4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)-2,3-diacetamido-6-O-benzyl-2,3-dideoxy-α-D-mannopyranoside 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:
-
ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-α-D-glucopyranoside; 2-(p-trifluoroacetamidophenyl)ethyl 2,3-diazido-6-O-benzyl-2,3-dideoxy-α-D-mannopyranoside;
With
2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate;
In
dichloromethane;
at 20 ℃;
for 14h;
With
hydrogen sulfide; triethylamine;
In
pyridine; water;
for 1.91667h;
acetic anhydride;
In
pyridine;
for 1.5h;
DOI:10.1016/S0008-6215(99)00318-3
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 50 percent / pyridine / 70 h / 20 °C
2.1: Bu4NHSO4; NaOH; K2CO3 / toluene; dimethylsulfoxide; butan-1-ol / 2 h / 20 °C
3.1: NaN3; NH4Cl / dimethylsulfoxide / 20 h / 80 °C
4.1: CH2Cl2; pyridine / 2.5 h / 0 - 20 °C
5.1: NaN3 / dimethylsulfoxide / 0.5 h / 20 °C
6.1: 44 percent / 4 Angstroem molecular sieves; dimethyl(thiomethyl)sulfonium triflate / CH2Cl2 / 70 h / 20 °C
7.1: 73 percent / sodium cyanoborohydride; 3 Angstroem molecular sieves; fluoroboric acid / tetrahydrofuran; diethyl ether / 4 h / 0 °C
8.1: 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves; dimethyl(thiomethyl)sulfonium triflate / CH2Cl2 / 14 h / 20 °C
8.2: H2S; Et3N / pyridine; H2O / 1.92 h
8.3: 40 percent / pyridine / 1.5 h
With
sodium hydroxide; tetrafluoroboric acid; sodium azide; 2,6-di-tert-butyl-4-methylpyridine; 3 A molecular sieve; 4 A molecular sieve; tetra(n-butyl)ammonium hydrogensulfate; sodium cyanoborohydride; potassium carbonate; ammonium chloride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate;
In
tetrahydrofuran; pyridine; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; butan-1-ol;
1.1: Tosylation / 2.1: Substitution / 3.1: Substitution / 4.1: Acylation / 5.1: Substitution / 6.1: glycosylation / 7.1: Reduction / 8.1: glycosylation / 8.2: Reduction / 8.3: Acetylation;
DOI:10.1016/S0008-6215(99)00318-3
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: 44 percent / 4 Angstroem molecular sieves; dimethyl(thiomethyl)sulfonium triflate / CH2Cl2 / 70 h / 20 °C
2.1: 73 percent / sodium cyanoborohydride; 3 Angstroem molecular sieves; fluoroboric acid / tetrahydrofuran; diethyl ether / 4 h / 0 °C
3.1: 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves; dimethyl(thiomethyl)sulfonium triflate / CH2Cl2 / 14 h / 20 °C
3.2: H2S; Et3N / pyridine; H2O / 1.92 h
3.3: 40 percent / pyridine / 1.5 h
With
tetrafluoroboric acid; 2,6-di-tert-butyl-4-methylpyridine; 3 A molecular sieve; 4 A molecular sieve; sodium cyanoborohydride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate;
In
tetrahydrofuran; diethyl ether; dichloromethane;
1.1: glycosylation / 2.1: Reduction / 3.1: glycosylation / 3.2: Reduction / 3.3: Acetylation;
DOI:10.1016/S0008-6215(99)00318-3
