Technology Process of (1S,2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)cyclohexane-1,2-diol
There total 12 articles about (1S,2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)cyclohexane-1,2-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:
- Guidance literature:
-
(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-6-hydroxymethyl-cyclohexanone;
With
diisobutylaluminium hydride;
In
toluene;
at -78 ℃;
for 0.5h;
With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
at 20 ℃;
for 4h;
DOI:10.1021/ol035424n
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: NaH / dimethylformamide / 2 h / 20 °C
1.2: 88 percent / dimethylformamide / 12 h / 20 °C
2.1: BH3*Me2S / CH2Cl2 / 3 h / 20 °C
2.2: 68 percent / BF3*OEt2 / CH2Cl2 / 0.5 h / 20 °C
3.1: 90 percent / Ph3P; CBr4 / CH2Cl2 / 2 h / 20 °C
4.1: Zn / aq. ethanol / 0.5 h / 90 °C
5.1: 59 percent / 1,1,3,3-tetramethylguanidine / tetrahydrofuran / 12 h / 20 °C
6.1: Me3SiCl; DMAP; Et3N / acetonitrile / 12 h / 20 °C
6.2: 54 percent / p-TsOH / acetonitrile / 3 h / 20 °C
7.1: 95 percent / Et3N / CH2Cl2 / 12 h / 20 °C
8.1: 20 mg / Mo(CO)6 / acetonitrile; H2O / 1.5 h / 90 °C
9.1: DIBALH / toluene / 0.5 h / -78 °C
9.2: 10 mg / TBAF / tetrahydrofuran / 4 h / 20 °C
With
dmap; chloro-trimethyl-silane; hexacarbonyl molybdenum; carbon tetrabromide; dimethylsulfide borane complex; sodium hydride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; zinc; N,N,N',N'-tetramethylguanidine;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
5.1: Henry reaction;
DOI:10.1021/ol035424n
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 90 percent / Ph3P; CBr4 / CH2Cl2 / 2 h / 20 °C
2.1: Zn / aq. ethanol / 0.5 h / 90 °C
3.1: 59 percent / 1,1,3,3-tetramethylguanidine / tetrahydrofuran / 12 h / 20 °C
4.1: Me3SiCl; DMAP; Et3N / acetonitrile / 12 h / 20 °C
4.2: 54 percent / p-TsOH / acetonitrile / 3 h / 20 °C
5.1: 95 percent / Et3N / CH2Cl2 / 12 h / 20 °C
6.1: 20 mg / Mo(CO)6 / acetonitrile; H2O / 1.5 h / 90 °C
7.1: DIBALH / toluene / 0.5 h / -78 °C
7.2: 10 mg / TBAF / tetrahydrofuran / 4 h / 20 °C
With
dmap; chloro-trimethyl-silane; hexacarbonyl molybdenum; carbon tetrabromide; diisobutylaluminium hydride; triethylamine; triphenylphosphine; zinc; N,N,N',N'-tetramethylguanidine;
In
tetrahydrofuran; ethanol; dichloromethane; water; toluene; acetonitrile;
3.1: Henry reaction;
DOI:10.1021/ol035424n
