Technology Process of (1R,2R,3S,6S,7R,8S,9S,12R,14R)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.01,8]tetradecane-6,12-diol
There total 14 articles about (1R,2R,3S,6S,7R,8S,9S,12R,14R)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.01,8]tetradecane-6,12-diol 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:
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![(1R,2R,3S,7R,8S,9S,14R)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.0<sup>1,8</sup>]tetradecane-6,12-dione](/Databaselist/images/loading.webp)
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80878-29-1
(1R,2R,3S,7R,8S,9S,14R)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.01,8]tetradecane-6,12-dione
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80878-30-4
(1R,2R,3S,6S,7R,8S,9S,12R,14R)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.01,8]tetradecane-6,12-diol
- Guidance literature:
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With
diisobutylaluminium hydride;
In
dichloromethane;
at -60 ℃;
for 0.166667h;
Yield given;
DOI:10.1021/ja00370a067
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80878-30-4
(1R,2R,3S,6S,7R,8S,9S,12R,14R)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.01,8]tetradecane-6,12-diol
- Guidance literature:
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Multi-step reaction with 14 steps
1: 67 percent / tetrahydrofuran; diethyl ether / -40 °C
2: 79 percent / PCC / CH2Cl2
3: 82 percent / tetrahydrofuran / -93 - -80 °C
4: 88 percent / MnO2 / CH2Cl2
5: 61 percent / hydrogen / 10percent Pd/Al2O3, MnO / various solvent(s); ethyl acetate / 760 Torr
6: 92 percent / K2CO3 / methanol
7: POCl3, DMAP / CH2Cl2; pyridine / 35 °C
8: 80 percent / CF3COOH / CH2Cl2 / Ambient temperature
9: 97 percent / t-BuOOH, VO(acac)2 / benzene / Ambient temperature
10: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / -30 °C
11: 71 percent / KH / dimethylformamide; tetrahydrofuran / -30 - -20 °C
12: N-bromoacetamide, NaOAc / methanol; H2O / 8.5 h / 25 °C
13: 81 percent / zinc dust, HOAc / methanol / 0.75 h / -20 °C
14: DIBAH / CH2Cl2 / 0.17 h / -60 °C
With
tert.-butylhydroperoxide; dmap; manganese(IV) oxide; bis(acetylacetonate)oxovanadium; potassium tert-butylate; hydrogen; sodium acetate; potassium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; pyridinium chlorochromate; trifluoroacetic acid; zinc; trichlorophosphate; N-bromoacetamide;
palladium/alumina; manganese(II) oxide;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1021/ja00370a067
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80878-30-4
(1R,2R,3S,6S,7R,8S,9S,12R,14R)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.01,8]tetradecane-6,12-diol
- Guidance literature:
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Multi-step reaction with 13 steps
1: 79 percent / PCC / CH2Cl2
2: 82 percent / tetrahydrofuran / -93 - -80 °C
3: 88 percent / MnO2 / CH2Cl2
4: 61 percent / hydrogen / 10percent Pd/Al2O3, MnO / various solvent(s); ethyl acetate / 760 Torr
5: 92 percent / K2CO3 / methanol
6: POCl3, DMAP / CH2Cl2; pyridine / 35 °C
7: 80 percent / CF3COOH / CH2Cl2 / Ambient temperature
8: 97 percent / t-BuOOH, VO(acac)2 / benzene / Ambient temperature
9: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / -30 °C
10: 71 percent / KH / dimethylformamide; tetrahydrofuran / -30 - -20 °C
11: N-bromoacetamide, NaOAc / methanol; H2O / 8.5 h / 25 °C
12: 81 percent / zinc dust, HOAc / methanol / 0.75 h / -20 °C
13: DIBAH / CH2Cl2 / 0.17 h / -60 °C
With
tert.-butylhydroperoxide; dmap; manganese(IV) oxide; bis(acetylacetonate)oxovanadium; potassium tert-butylate; hydrogen; sodium acetate; potassium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; pyridinium chlorochromate; trifluoroacetic acid; zinc; trichlorophosphate; N-bromoacetamide;
palladium/alumina; manganese(II) oxide;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1021/ja00370a067
