Technology Process of (2S,3R,4R,5R,6R)-4-hydroxy-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
There total 15 articles about (2S,3R,4R,5R,6R)-4-hydroxy-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 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
hydrogen;
palladium on activated charcoal;
In
methanol;
at 20 ℃;
for 4h;
DOI:10.1021/ol0501875
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 86.8 percent / TMSOTf / CH2Cl2 / -50 °C
2: 10 percent / aq. EDTA; 1,1,1-trifluoroacetone; Oxone(R) / NaHCO3 / acetonitrile / 2 h / -20 °C
3: 69 percent / K2CO3 / methanol / 20 °C
4: 91 percent / DMSO; oxalyl chloride; Et3N / CH2Cl2 / -78 - 20 °C
5: 90 percent / CeCl3*7H2O; NaBH4 / methanol / -78 - 20 °C
6: 99 percent / H2 / Pd/C / methanol / 4 h / 20 °C
With
sodium tetrahydroborate; cerium(III) chloride; oxone; oxalyl dichloride; ethylenediaminetetraacetic acid; 1,1,1-trifluoro-2-propanone; trimethylsilyl trifluoromethanesulfonate; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine;
palladium on activated charcoal; sodium hydrogencarbonate;
In
methanol; dichloromethane; acetonitrile;
DOI:10.1021/ol0501875
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: DCC; DMAP / toluene / 0 - 20 °C
2.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C
2.2: TMSCl / tetrahydrofuran / -78 - 20 °C
3.1: NaHCO3; adogen-464 / CH2Cl2 / 20 °C
4.1: DDQ / CH2Cl2; H2O / 0 - 20 °C
5.1: 2,6-lutidine / CH2Cl2 / 2 h / 0 °C
6.1: 86.8 percent / TMSOTf / CH2Cl2 / -50 °C
7.1: 10 percent / aq. EDTA; 1,1,1-trifluoroacetone; Oxone(R) / NaHCO3 / acetonitrile / 2 h / -20 °C
8.1: 69 percent / K2CO3 / methanol / 20 °C
9.1: 91 percent / DMSO; oxalyl chloride; Et3N / CH2Cl2 / -78 - 20 °C
10.1: 90 percent / CeCl3*7H2O; NaBH4 / methanol / -78 - 20 °C
11.1: 99 percent / H2 / Pd/C / methanol / 4 h / 20 °C
With
2,6-dimethylpyridine; dmap; sodium tetrahydroborate; cerium(III) chloride; oxone; oxalyl dichloride; ethylenediaminetetraacetic acid; 1,1,1-trifluoro-2-propanone; trimethylsilyl trifluoromethanesulfonate; Adogen-464; hydrogen; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane;
palladium on activated charcoal; sodium hydrogencarbonate;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/ol0501875
