Technology Process of Benzoic acid (1S,2R,3R,4S,5R,6S)-2,3,4-tris-benzyloxy-6-(1-ethoxy-ethoxy)-5-fluoro-cyclohexyl ester
There total 8 articles about Benzoic acid (1S,2R,3R,4S,5R,6S)-2,3,4-tris-benzyloxy-6-(1-ethoxy-ethoxy)-5-fluoro-cyclohexyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 53 percent / (diethylamido)sulfur trifluoride / CH2Cl2 / 1.) -40 dec C to -30 deg C, 30 min, 2.) -20 deg C, 2.5 h, 3.) 0 deg C, 2.8 h then r.t., 30 min
2: 99 percent / BBr3 / CH2Cl2 / 19 h / Ambient temperature
3: 2.) acetyl chloride / 1.) camphorsulfonic acid / 1.) DMF, 80 deg C, 4 h, 2.) CH2Cl2, MeOH, 23 deg C, 1 h
4: 96 percent / NaH / dimethylformamide / 1.) ice bath temp., 3 h, 2.) 8-10 deg C, then r.t., 3 h
5: 100 percent / aq. conc. HCl / methanol / 21 h / Ambient temperature
6: pyridine / 0 °C
7: camphorsulfonic acid / CH2Cl2 / 0 °C
With
pyridine; (diethylamido)sulfur trifluoride; boron tribromide; sodium hydride; acetyl chloride;
hydrogenchloride; camphor-10-sulfonic acid;
In
methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00084a010
- Guidance literature:
-
Multi-step reaction with 5 steps
1: 2.) acetyl chloride / 1.) camphorsulfonic acid / 1.) DMF, 80 deg C, 4 h, 2.) CH2Cl2, MeOH, 23 deg C, 1 h
2: 96 percent / NaH / dimethylformamide / 1.) ice bath temp., 3 h, 2.) 8-10 deg C, then r.t., 3 h
3: 100 percent / aq. conc. HCl / methanol / 21 h / Ambient temperature
4: pyridine / 0 °C
5: camphorsulfonic acid / CH2Cl2 / 0 °C
With
pyridine; sodium hydride; acetyl chloride;
hydrogenchloride; camphor-10-sulfonic acid;
In
methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00084a010
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 99 percent / BBr3 / CH2Cl2 / 19 h / Ambient temperature
2: 2.) acetyl chloride / 1.) camphorsulfonic acid / 1.) DMF, 80 deg C, 4 h, 2.) CH2Cl2, MeOH, 23 deg C, 1 h
3: 96 percent / NaH / dimethylformamide / 1.) ice bath temp., 3 h, 2.) 8-10 deg C, then r.t., 3 h
4: 100 percent / aq. conc. HCl / methanol / 21 h / Ambient temperature
5: pyridine / 0 °C
6: camphorsulfonic acid / CH2Cl2 / 0 °C
With
pyridine; boron tribromide; sodium hydride; acetyl chloride;
hydrogenchloride; camphor-10-sulfonic acid;
In
methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00084a010
