Technology Process of C-[(2S,3R,4R,5R)-cyclohex-1-ene-5,6-ethane-2,3,4,5,6-pentaol]methylphosphonic acid
There total 2 articles about C-[(2S,3R,4R,5R)-cyclohex-1-ene-5,6-ethane-2,3,4,5,6-pentaol]methylphosphonic acid which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(2S,3R,4R,5R)-2,3-bis(benzyloxy)-1-(dimethoxyphosphoryl)methyl-4-hydroxy cyclohex-1-ene-ethane-5,6-diol-O-isopropylidene;
With
trimethylsilyl bromide;
In
dichloromethane;
at 20 ℃;
for 2.5h;
Inert atmosphere;
With
hydrogen; palladium(II) hydroxide;
In
methanol; ethyl acetate;
for 0.333333h;
Inert atmosphere;
DOI:10.1021/ol500848q
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 6 h / 80 °C / Inert atmosphere
2.1: tetra-n-butylammoniumfluoride trihydrate / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
3.1: zinc dibromide / 2 h / 25 - 100 °C / Inert atmosphere; Microwave irradiation
4.1: trimethylsilyl bromide / dichloromethane / 2.5 h / 20 °C / Inert atmosphere
4.2: 0.33 h / Inert atmosphere
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; trimethylsilyl bromide; tetra-n-butylammoniumfluoride trihydrate; zinc dibromide;
In
tetrahydrofuran; dichloromethane; toluene;
3.1: |Michaelis-Arbuzov Synthesis;
DOI:10.1021/ol500848q
- Guidance literature:
-
C-[(2S,3R,4R,5R)-cyclohex-1-ene-5,6-ethane-2,3,4,5,6-pentaol]methylphosphonic acid;
In
water;
for 0.5h;
UMP triethylammonium salt;
With
N,N-dimethyl-aniline; triethylamine;
In
acetonitrile;
at 0 ℃;
for 0.583333h;
Further stages;
Molecular sieve;
Inert atmosphere;
DOI:10.1021/ol500848q
