Technology Process of (3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
There total 1 articles about (3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(5-bromo-2-chlorobenzyloxy)(tert-butyl)diphenylsilane; (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one;
With
tert.-butyl lithium;
In
tetrahydrofuran;
at -78 ℃;
for 5h;
methanol;
With
methanesulfonic acid;
In
tetrahydrofuran;
at -78 - 20 ℃;
DOI:10.1016/j.bmc.2014.04.036
- Guidance literature:
-
Multi-step reaction with 4 steps
1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C
2: pyridine; dmap / chloroform / 20 °C
3: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C
4: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere
With
pyridine; triethylsilane; dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; dichloromethane; chloroform;
4: |Mitsunobu Displacement;
DOI:10.1016/j.bmc.2014.04.036
- Guidance literature:
-
Multi-step reaction with 5 steps
1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C
2: pyridine; dmap / chloroform / 20 °C
3: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C
4: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere
5: tetrabutyl ammonium fluoride / tetrahydrofuran
With
pyridine; triethylsilane; dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; dichloromethane; chloroform;
4: |Mitsunobu Displacement;
DOI:10.1016/j.bmc.2014.04.036