Technology Process of (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,6S)-6,7-dihydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
There total 44 articles about (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,6S)-6,7-dihydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
cation exchange resin ( AG 50W-X4,200-400 mesh );
In
methanol;
for 16h;
Ambient temperature;
DOI:10.1016/0040-4020(84)80011-3
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 1.) LAH; 2.) 10 percent NaOH / 1.) THF, 20 deg C, 0.5 h, rt, 15 min; reflux 2 h; 2.) water, 15 deg C, 0.25 h
2: 2.2 g / toluenesulfonic acid monohydrate / acetone / 25 h / Ambient temperature
3: 2.97 g / diethyl ether / 19 h / Ambient temperature
4: KOH / ethanol / 23 h / Heating
5: 1.) toluenesulfonic acid monohydrate; 2.) MeOH / 1.) RT, 50 min; 2.) RT, 45 min
6: H2 / 10 percent Pd/C / ethyl acetate
7: 90 percent / 2,2'- bipyridinium chlorochromate, anhyd. NaOAc / CH2Cl2 / 4.5 h / Ambient temperature
8: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min; 2.) THF, -78 deg C, 2,5 h
9: 86 percent / cation exchange resin ( AG 50W-X4,200-400 mesh ) / methanol / 16 h / Ambient temperature
With
methanol; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; cation exchange resin ( AG 50W-X4,200-400 mesh ); hydrogen; sodium acetate; toluene-4-sulfonic acid; 2,2'-bipyridinium chlorochromate;
palladium on activated charcoal; toluene-4-sulfonic acid;
In
methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; acetone;
DOI:10.1016/0040-4020(84)80011-3
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 2.2 g / toluenesulfonic acid monohydrate / acetone / 25 h / Ambient temperature
2: 2.97 g / diethyl ether / 19 h / Ambient temperature
3: KOH / ethanol / 23 h / Heating
4: 1.) toluenesulfonic acid monohydrate; 2.) MeOH / 1.) RT, 50 min; 2.) RT, 45 min
5: H2 / 10 percent Pd/C / ethyl acetate
6: 90 percent / 2,2'- bipyridinium chlorochromate, anhyd. NaOAc / CH2Cl2 / 4.5 h / Ambient temperature
7: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min; 2.) THF, -78 deg C, 2,5 h
8: 86 percent / cation exchange resin ( AG 50W-X4,200-400 mesh ) / methanol / 16 h / Ambient temperature
With
methanol; potassium hydroxide; n-butyllithium; cation exchange resin ( AG 50W-X4,200-400 mesh ); hydrogen; sodium acetate; toluene-4-sulfonic acid; 2,2'-bipyridinium chlorochromate;
palladium on activated charcoal; toluene-4-sulfonic acid;
In
methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; acetone;
DOI:10.1016/0040-4020(84)80011-3