Technology Process of 1,5-Anhydro-2,4,6,8-tetradeoxy-9-O-<(1,1-dimethylethyl)-diphenylsilyl>-2,4,6,8-tetramethyl-7-O-(phenylmethyl)-L-glycero-D-gulo-non-1-en-3-ulose (Pyrone 11)
There total 8 articles about 1,5-Anhydro-2,4,6,8-tetradeoxy-9-O-<(1,1-dimethylethyl)-diphenylsilyl>-2,4,6,8-tetramethyl-7-O-(phenylmethyl)-L-glycero-D-gulo-non-1-en-3-ulose (Pyrone 11) 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
boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate;
In
dichloromethane; benzene;
1) -78 deg C, 40 min, 2) reflux, 1h;
DOI:10.1021/jo00292a045
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 78 percent / 1) cerium trichloride heptahydrate, NaBH4, 2) p-toluene sulfonic acid / ethanol / 1) -15 deg C, 2) r.t., 1h
2: 80 percent / borane-dimethyl sulfide complex, NaOH, 30percent H2O2 / tetrahydrofuran; dimethylsulfoxide / 4 h
3: 64 percent / TiCl4 / CH2Cl2 / 1) 0 deg C, 2) r.t., 1.5h
4: 88 percent / Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 12 h / Ambient temperature
5: 100 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 8 h / Heating
6: NBS, NaHCO3 / acetone; H2O / -15 °C
7: 40 percent / 1) BF3 etherate, 2) pyridinium p-toluenesulfonate / CH2Cl2; benzene / 1) -78 deg C, 40 min, 2) reflux, 1h
With
dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; cerium(III) chloride; dimethylsulfide borane complex; boron trifluoride diethyl etherate; dihydrogen peroxide; pyridinium p-toluenesulfonate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine;
In
tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; acetone; benzene;
DOI:10.1021/jo00292a045
- Guidance literature:
-
Multi-step reaction with 5 steps
1: 64 percent / TiCl4 / CH2Cl2 / 1) 0 deg C, 2) r.t., 1.5h
2: 88 percent / Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 12 h / Ambient temperature
3: 100 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 8 h / Heating
4: NBS, NaHCO3 / acetone; H2O / -15 °C
5: 40 percent / 1) BF3 etherate, 2) pyridinium p-toluenesulfonate / CH2Cl2; benzene / 1) -78 deg C, 40 min, 2) reflux, 1h
With
dmap; N-Bromosuccinimide; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; triethylamine;
In
tetrahydrofuran; dichloromethane; water; acetone; benzene;
DOI:10.1021/jo00292a045
