Technology Process of {(2S,3S)-3-[(2S,3R,5R,7S)-8-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-3,5,7-trimethyl-octyl]-2-methyl-oxiranyl}-methanol
There total 13 articles about {(2S,3S)-3-[(2S,3R,5R,7S)-8-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-3,5,7-trimethyl-octyl]-2-methyl-oxiranyl}-methanol 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
titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate;
In
dichloromethane;
at -23 ℃;
DOI:10.1021/ol0100069
- Guidance literature:
-
Multi-step reaction with 12 steps
1: iodine; triphenylphosphine; imidazole / CH2Cl2 / 23 °C
2: 1.66 g / n-BuLi; TMEDA / diethyl ether / -78 °C
3: 747 mg / O3; triphenylphosphine / CH2Cl2 / 4 h / 23 °C
4: NaH / tetrahydrofuran / 23 °C
5: 740 g / diisobutylaluminium hydride / CH2Cl2; various solvent(s) / -40 °C
6: 90 percent / (-)-DET; Ti(OiPr)4; TBHP / CH2Cl2 / 20 h / -23 °C
7: oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 °C
8: 0.6 percent / benzene / 15 h / 80 °C
9: 90 percent / n-Bu3P; formic acid; triethylamine / Pd2(dba)3*CHCl3 / dioxane / 10 h / 23 °C
10: triethylamine / CH2Cl2
11: 5.23 g / DIBAL-H / CH2Cl2 / -40 °C
12: 91 percent / Ti(OiPr)4; (+)-DET; TBHP / CH2Cl2 / -23 °C
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; formic acid; oxalyl dichloride; diethyl (2R,3R)-tartrate; N,N,N,N,-tetramethylethylenediamine; tributylphosphine; iodine; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; triphenylphosphine;
tris(dibenzylideneacetone)dipalladium(0) chloroform complex;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; benzene;
4: Horner-Emmons olefination / 6: Sharpless asymmetric epoxidation / 7: Swern oxidation / 8: Wittig homologation / 12: Sharpless epoxidation;
DOI:10.1021/ol0100069
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 1.66 g / n-BuLi; TMEDA / diethyl ether / -78 °C
2: 747 mg / O3; triphenylphosphine / CH2Cl2 / 4 h / 23 °C
3: NaH / tetrahydrofuran / 23 °C
4: 740 g / diisobutylaluminium hydride / CH2Cl2; various solvent(s) / -40 °C
5: 90 percent / (-)-DET; Ti(OiPr)4; TBHP / CH2Cl2 / 20 h / -23 °C
6: oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 °C
7: 0.6 percent / benzene / 15 h / 80 °C
8: 90 percent / n-Bu3P; formic acid; triethylamine / Pd2(dba)3*CHCl3 / dioxane / 10 h / 23 °C
9: triethylamine / CH2Cl2
10: 5.23 g / DIBAL-H / CH2Cl2 / -40 °C
11: 91 percent / Ti(OiPr)4; (+)-DET; TBHP / CH2Cl2 / -23 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; formic acid; oxalyl dichloride; diethyl (2R,3R)-tartrate; N,N,N,N,-tetramethylethylenediamine; tributylphosphine; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; triphenylphosphine;
tris(dibenzylideneacetone)dipalladium(0) chloroform complex;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; benzene;
3: Horner-Emmons olefination / 5: Sharpless asymmetric epoxidation / 6: Swern oxidation / 7: Wittig homologation / 11: Sharpless epoxidation;
DOI:10.1021/ol0100069
