Technology Process of benzyl (E)-3-<(2R,3S)-3-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-yl>propenoate
There total 10 articles about benzyl (E)-3-<(2R,3S)-3-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-yl>propenoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
for 3h;
Ambient temperature;
DOI:10.1021/ja00164a026
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 95 percent / H2 / 5percent Pd/C / methanol / 16 h / 25 °C
2: 92 percent / imidazole / dimethylformamide / 16 h / 25 °C
3: 72 percent / trifluoroacetic acid / tetrahydrofuran; H2O / 0.17 h / 0 °C
4: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C
5: benzene / 3 h / Ambient temperature
6: 88 percent / LiOH / tetrahydrofuran; H2O / 5 h / 50 °C
7: 82 percent / 1,3-dicyclohexylcarbodiimide (DCC), 4-(dimethylamino)pyridine (DMAP), camphorsulfonic acid (CSA) / CH2Cl2 / 6 h / 25 °C
8: 88 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature
With
1H-imidazole; dmap; lithium hydroxide; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00164a026
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 95 percent / NaOMe / methanol / 2 h / 25 °C
2: 95 percent / H2 / 5percent Pd/C / methanol / 16 h / 25 °C
3: 92 percent / imidazole / dimethylformamide / 16 h / 25 °C
4: 72 percent / trifluoroacetic acid / tetrahydrofuran; H2O / 0.17 h / 0 °C
5: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C
6: benzene / 3 h / Ambient temperature
7: 88 percent / LiOH / tetrahydrofuran; H2O / 5 h / 50 °C
8: 82 percent / 1,3-dicyclohexylcarbodiimide (DCC), 4-(dimethylamino)pyridine (DMAP), camphorsulfonic acid (CSA) / CH2Cl2 / 6 h / 25 °C
9: 88 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature
With
1H-imidazole; dmap; lithium hydroxide; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00164a026
