Technology Process of Spiro[oxirane-2,1'(2'H)-pentaleno[1,6a-c]pyran]-5'-carboxylicacid, 4',4'a,6'a,7',8',9'-hexahydro-8',8'-dimethyl-2'-oxo-,(1'S,4'aR,6'aS,9'aR)- (9CI)
There total 17 articles about Spiro[oxirane-2,1'(2'H)-pentaleno[1,6a-c]pyran]-5'-carboxylicacid, 4',4'a,6'a,7',8',9'-hexahydro-8',8'-dimethyl-2'-oxo-,(1'S,4'aR,6'aS,9'aR)- (9CI) 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:
-
pentalenolactone F methyl ester;
With
water; potassium carbonate;
In
methanol;
for 24h;
Reflux;
With
hydrogenchloride;
In
water;
pH=2;
DOI:10.1021/ja111279h
- Guidance literature:
-
Multi-step reaction with 12 steps
1: 71 percent / hydroboration-oxidation
2: 87 percent / 15 h / 85 °C
3: 86 percent / SeO2 / ethanol / 24 h / Heating
4: NaCN/MnO2/AcOH / room temp., 18 h
5: 78 percent / 0 °C / Jones oxidation
6: 1.) TMSOTf, Et3N; 2.) NBS / 1.) benzene, room temp., 10 min; 2.) THF, 5 min
7: 30 percent / Et3N, NaHCO3 / benzene / 24 h / Ambient temperature
8: 80 percent / (TMS)2NH / benzene / 2 h / Ambient temperature
9: 1.) mCPBA; 2.) NaIO4 / 1.) hexane, - 15 deg C, 30 min; room temp., 2h; 2.) H2O-t-BuOH, room temp., 4h
10: 1.) NaBH4; 2.) 2N HCl / 1.) EtOH, 0 degC, 10 min; 2.) pH 2, room temp., 2 h
11: 40 percent / 30percent H2O2 / methanol; H2O / 24 h / Ambient temperature
12: 1.) LiOH; 2.) 1N HCl / 1.) H2O-THF, room temp.; 2.) pH 2, room temp., 2 h
With
hydrogenchloride; manganese(IV) oxide; lithium hydroxide; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; selenium(IV) oxide; trimethylsilyl trifluoromethanesulfonate; sodium cyanide; dihydrogen peroxide; sodium hydrogencarbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane;
In
methanol; ethanol; water; benzene;
DOI:10.1016/S0040-4039(00)94293-X
-
![(1R,2R,3aR,4S,5aR,8aS)-1,4,7,7-Tetramethyl-octahydro-cyclopenta[c]pentalene-2,3a-diol](/Databaselist/images/loading.webp)
-
89111-52-4,89163-66-6
(1R,2R,3aR,4S,5aR,8aS)-1,4,7,7-Tetramethyl-octahydro-cyclopenta[c]pentalene-2,3a-diol
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 87 percent / 15 h / 85 °C
2: 86 percent / SeO2 / ethanol / 24 h / Heating
3: NaCN/MnO2/AcOH / room temp., 18 h
4: 78 percent / 0 °C / Jones oxidation
5: 1.) TMSOTf, Et3N; 2.) NBS / 1.) benzene, room temp., 10 min; 2.) THF, 5 min
6: 30 percent / Et3N, NaHCO3 / benzene / 24 h / Ambient temperature
7: 80 percent / (TMS)2NH / benzene / 2 h / Ambient temperature
8: 1.) mCPBA; 2.) NaIO4 / 1.) hexane, - 15 deg C, 30 min; room temp., 2h; 2.) H2O-t-BuOH, room temp., 4h
9: 1.) NaBH4; 2.) 2N HCl / 1.) EtOH, 0 degC, 10 min; 2.) pH 2, room temp., 2 h
10: 40 percent / 30percent H2O2 / methanol; H2O / 24 h / Ambient temperature
11: 1.) LiOH; 2.) 1N HCl / 1.) H2O-THF, room temp.; 2.) pH 2, room temp., 2 h
With
hydrogenchloride; manganese(IV) oxide; lithium hydroxide; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; selenium(IV) oxide; trimethylsilyl trifluoromethanesulfonate; sodium cyanide; dihydrogen peroxide; sodium hydrogencarbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane;
In
methanol; ethanol; water; benzene;
DOI:10.1016/S0040-4039(00)94293-X
