Technology Process of E/Z-prop-2-enyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside
There total 10 articles about E/Z-prop-2-enyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 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:
-
Multi-step reaction with 6 steps
1: 13 g / DL-10-camphorsulfonic acid / acetonitrile / 12 h / 20 °C
2: 75 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 16 h
3: 79 percent / N-iodosuccinimide; triflic acid; 4A molecular sieves / CH2Cl2 / 0.17 h / 0 °C
4: 85 percent / Bu4NF / tetrahydrofuran / 20 h / 20 °C
5: 74 percent / 4A molecular sieves; trimethylsilyl trifluoromethanesulfonate / CH2Cl2 / 1 h / -40 - -10 °C
6: 77 percent / RuCl2(=CHPh)(PCy3)(1,3-dimesityl-4,5-dihydroimidazolylidene) / CH2Cl2 / 2 h / 20 °C
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja0484045
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 0.044 g / BF3*Et2O / CH2Cl2 / 3 h / 20 °C
2: NaOMe / CH2Cl2; methanol / 2 h / 20 °C
3: 13 g / DL-10-camphorsulfonic acid / acetonitrile / 12 h / 20 °C
4: 75 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 16 h
5: 79 percent / N-iodosuccinimide; triflic acid; 4A molecular sieves / CH2Cl2 / 0.17 h / 0 °C
6: 85 percent / Bu4NF / tetrahydrofuran / 20 h / 20 °C
7: 74 percent / 4A molecular sieves; trimethylsilyl trifluoromethanesulfonate / CH2Cl2 / 1 h / -40 - -10 °C
8: 77 percent / RuCl2(=CHPh)(PCy3)(1,3-dimesityl-4,5-dihydroimidazolylidene) / CH2Cl2 / 2 h / 20 °C
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja0484045
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 13 g / DL-10-camphorsulfonic acid / acetonitrile / 12 h / 20 °C
2: 75 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 16 h
3: 79 percent / N-iodosuccinimide; triflic acid; 4A molecular sieves / CH2Cl2 / 0.17 h / 0 °C
4: 85 percent / Bu4NF / tetrahydrofuran / 20 h / 20 °C
5: 74 percent / 4A molecular sieves; trimethylsilyl trifluoromethanesulfonate / CH2Cl2 / 1 h / -40 - -10 °C
6: 77 percent / RuCl2(=CHPh)(PCy3)(1,3-dimesityl-4,5-dihydroimidazolylidene) / CH2Cl2 / 2 h / 20 °C
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja0484045