Technology Process of (1R,2R,3S,6R)-6-(azidomethyl)cyclohex-4-ene-1,2,3-triyl tribenzoate
There total 6 articles about (1R,2R,3S,6R)-6-(azidomethyl)cyclohex-4-ene-1,2,3-triyl tribenzoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(1R,2R,5S,6S)-2-(azidomethyl)-5,6-bis(benzyloxy)cyclohex-3-enol;
With
boron trichloride;
In
dichloromethane;
at -78 ℃;
for 6h;
benzoyl chloride;
With
pyridine;
at 0 - 20 ℃;
for 18h;
- Guidance literature:
-
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid; triethylamine / dichloromethane / 5 h / 0 °C
1.2: 24 h / 60 °C
2.1: boron trichloride / dichloromethane / 6 h / -78 °C
2.2: 18 h / 0 - 20 °C
With
boron trichloride; toluene-4-sulfonic acid; triethylamine;
In
dichloromethane;
- Guidance literature:
-
Multi-step reaction with 7 steps
1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / 40 °C / Darkness; Inert atmosphere
2: diisobutylaluminium hydride / tetrahydrofuran; hexane / 2.5 h / 0 - 20 °C / Inert atmosphere
3: sodium tetrahydroborate / water; ethyl acetate / 18 h / 0 - 20 °C / Inert atmosphere
4: triethylamine; p-toluenesulfonyl chloride / dichloromethane / 5 h / 40 °C / Inert atmosphere
5: sodium azide / N,N-dimethyl-formamide / 24 h / 60 °C / Inert atmosphere
6: boron trichloride / dichloromethane / 6 h / -78 - -60 °C / Inert atmosphere
7: pyridine / 18 h / 0 - 20 °C / Inert atmosphere
With
pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium tetrahydroborate; sodium azide; boron trichloride; diisobutylaluminium hydride; triethylamine; p-toluenesulfonyl chloride;
In
tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201402588
