Technology Process of (3S,4R,5S,6R)-6-(benzyloxymethyl)-3,4,5-(tribenzyloxy)cyclohex-1-ene
There total 6 articles about (3S,4R,5S,6R)-6-(benzyloxymethyl)-3,4,5-(tribenzyloxy)cyclohex-1-ene which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(3S,4S,5S,6R)-6-(hydroxymethyl)-3,4-dibenzyloxy-5-hydroxycyclohex-1-ene;
With
sodium hydride;
In
N,N-dimethyl-formamide; mineral oil;
at 5 ℃;
Inert atmosphere;
benzyl bromide;
In
N,N-dimethyl-formamide; mineral oil;
at 20 ℃;
for 6h;
Inert atmosphere;
DOI:10.1021/ja202610x
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: triethylamine; di-n-butylboron trifluoromethanesulphonate / dichloromethane / -78 - 0 °C / Inert atmosphere
1.2: 3 h / -78 - 15 °C / Inert atmosphere
2.1: lithium borohydride / tetrahydrofuran; diethyl ether; water / 0 - 20 °C / Inert atmosphere
3.1: 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
4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5 °C / Inert atmosphere
4.2: 6 h / 20 °C / Inert atmosphere
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium borohydride; sodium hydride; triethylamine; di-n-butylboron trifluoromethanesulphonate;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/ja202610x
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: lithium borohydride / tetrahydrofuran; water / 2 h / 0 - 20 °C
2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 20 h / 40 °C / Inert atmosphere; Darkness
2.2: 20 °C / Inert atmosphere
3.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium borohydride; tetra-(n-butyl)ammonium iodide; sodium hydride;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/ejoc.201402589
