Technology Process of Toluene-4-sulfonic acid (3R,3aS,6S,7R,8R,8aS)-7-hydroxy-8-methyl-octahydro-3a,6-methano-azulen-3-ylmethyl ester
There total 13 articles about Toluene-4-sulfonic acid (3R,3aS,6S,7R,8R,8aS)-7-hydroxy-8-methyl-octahydro-3a,6-methano-azulen-3-ylmethyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 10 steps
3: 1.) i-Pr2NLi 2.) HOAc / 1.) THF, -78 gradC 2.) Et2O, -78 gradC
4: 110 °C / 0.1 Torr
6: 1.) p-MeC6H4SO3H 2.) Ph3P-CCl4-Et3N / 1.) MeOH, reflux 2.) reflux
7: i-Pr2NLi / tetrahydrofuran / -78 °C
8: LiAlH4 / diethyl ether
9: 4-dimethylaminopyridine / CH2Cl2
10: 1.) BH3*Me2S 2.) H2O2, NaOH / 1.) THF
With
dmap; sodium hydroxide; lithium aluminium tetrahydride; dimethylsulfide borane complex; triphenylphosphine-carbon tetrachloride; dihydrogen peroxide; toluene-4-sulfonic acid; acetic acid; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(00)95593-X
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 36 percent / hydrozirconation-iodination
4: 1.) i-Pr2NLi 2.) HOAc / 1.) THF, -78 gradC 2.) Et2O, -78 gradC
5: 110 °C / 0.1 Torr
7: 1.) p-MeC6H4SO3H 2.) Ph3P-CCl4-Et3N / 1.) MeOH, reflux 2.) reflux
8: i-Pr2NLi / tetrahydrofuran / -78 °C
9: LiAlH4 / diethyl ether
10: 4-dimethylaminopyridine / CH2Cl2
11: 1.) BH3*Me2S 2.) H2O2, NaOH / 1.) THF
With
dmap; sodium hydroxide; lithium aluminium tetrahydride; dimethylsulfide borane complex; triphenylphosphine-carbon tetrachloride; dihydrogen peroxide; toluene-4-sulfonic acid; acetic acid; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(00)95593-X
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 1.) t-BuLi 2.) HOAc / 1.) THF-Et2O-pentane, -107 gradC 2.) Et2O, -107 gradC
4: 1.) i-Pr2NLi 2.) HOAc / 1.) THF, -78 gradC 2.) Et2O, -78 gradC
5: 110 °C / 0.1 Torr
7: 1.) p-MeC6H4SO3H 2.) Ph3P-CCl4-Et3N / 1.) MeOH, reflux 2.) reflux
8: i-Pr2NLi / tetrahydrofuran / -78 °C
9: LiAlH4 / diethyl ether
10: 4-dimethylaminopyridine / CH2Cl2
11: 1.) BH3*Me2S 2.) H2O2, NaOH / 1.) THF
With
dmap; sodium hydroxide; lithium aluminium tetrahydride; dimethylsulfide borane complex; triphenylphosphine-carbon tetrachloride; dihydrogen peroxide; tert.-butyl lithium; toluene-4-sulfonic acid; acetic acid; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(00)95593-X
