Technology Process of (2R,3R,4R,5R)-2,3-Bis-benzyloxy-3-methyl-5-trityloxy-tetrahydro-pyran-4-ol
There total 6 articles about (2R,3R,4R,5R)-2,3-Bis-benzyloxy-3-methyl-5-trityloxy-tetrahydro-pyran-4-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
5R,6R-bis-benxyloxy-5R-methyl-tetrahydro-pyran-3R,4R-diol;
With
di(n-butyl)tin oxide;
In
tetrahydrofuran;
for 1h;
Heating;
bromo-triphenyl-methane;
With
sodium hydroxide; tetra-(n-butyl)ammonium iodide;
In
N,N-dimethyl-formamide;
at 20 ℃;
for 3h;
With
sodium hydroxide;
In
diethyl ether; N,N-dimethyl-formamide;
for 1h;
DOI:10.1021/ja029225v
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: cerium trichloride / tetrahydrofuran; diethyl ether / 4 h / -20 °C
2.1: sodium hydride; imidazole / dimethylformamide / 0.33 h / 0 °C
2.2: dimethylformamide / 1 h / 20 °C
3.1: 38.65 g / (+/-)-camphorsulfonic acid / methanol / 1 h
4.1: di-n-butyltin oxide / tetrahydrofuran / 1 h / Heating
4.2: tetra-n-butylammonium iodide; sodium hydroxide / dimethylformamide / 3 h / 20 °C
4.3: 1.35 g / aq. NaOH / dimethylformamide; diethyl ether / 1 h
With
1H-imidazole; cerium(III) chloride; camphor-10-sulfonic acid; sodium hydride; di(n-butyl)tin oxide;
In
tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/ja029225v
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: (+/-)camphorsulfonic acid / acetone / 1 h / 25 °C
2.1: oxalyl chloride; dimethylsulfoxide; triethylamine / CH2Cl2 / -78 - 0 °C
3.1: cerium trichloride / tetrahydrofuran; diethyl ether / 4 h / -20 °C
4.1: sodium hydride; imidazole / dimethylformamide / 0.33 h / 0 °C
4.2: dimethylformamide / 1 h / 20 °C
5.1: 38.65 g / (+/-)-camphorsulfonic acid / methanol / 1 h
6.1: di-n-butyltin oxide / tetrahydrofuran / 1 h / Heating
6.2: tetra-n-butylammonium iodide; sodium hydroxide / dimethylformamide / 3 h / 20 °C
6.3: 1.35 g / aq. NaOH / dimethylformamide; diethyl ether / 1 h
With
1H-imidazole; cerium(III) chloride; oxalyl dichloride; (+/-)camphorsulfonic acid; camphor-10-sulfonic acid; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;
2.1: Swern oxidation;
DOI:10.1021/ja029225v
