Technology Process of (3R,5R,7S)-7-benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-8,8-dimethyl-nonane-3,5-diol
There total 9 articles about (3R,5R,7S)-7-benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-8,8-dimethyl-nonane-3,5-diol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
benzo[1,3,2]dioxaborole;
In
tetrahydrofuran;
at -10 ℃;
for 3h;
optical yield given as %de;
stereoselective reaction;
Inert atmosphere;
DOI:10.1021/jo101782q
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: pyridine; dmap / 0 - 20 °C / Inert atmosphere
2.1: borane-THF / tetrahydrofuran / -20 - 20 °C / Inert atmosphere
2.2: 1 h / Inert atmosphere
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 - -30 °C / Inert atmosphere
3.2: 0.5 h / -78 °C / Inert atmosphere
4.1: boron trifluoride diethyl etherate / dichloromethane / 1.25 h / -78 °C / Inert atmosphere
5.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 14 h / -40 - 20 °C / Inert atmosphere
With
pyridine; dmap; borane-THF; oxalyl dichloride; boron trifluoride diethyl etherate; acetic acid; dimethyl sulfoxide; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; dichloromethane; acetonitrile;
3.1: Swern oxidation / 3.2: Swern oxidation / 4.1: Mukaiyama reaction;
DOI:10.1021/jo101782q
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -78 °C / Inert atmosphere
1.2: Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / 0 °C / Inert atmosphere
2.2: 0 - 20 °C / Inert atmosphere
3.1: pyridine; dmap / 0 - 20 °C / Inert atmosphere
4.1: borane-THF / tetrahydrofuran / -20 - 20 °C / Inert atmosphere
4.2: 1 h / Inert atmosphere
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 - -30 °C / Inert atmosphere
5.2: 0.5 h / -78 °C / Inert atmosphere
6.1: boron trifluoride diethyl etherate / dichloromethane / 1.25 h / -78 °C / Inert atmosphere
7.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 14 h / -40 - 20 °C / Inert atmosphere
With
pyridine; dmap; n-butyllithium; borane-THF; oxalyl dichloride; boron trifluoride diethyl etherate; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; hexanes; dichloromethane; toluene; acetonitrile;
5.1: Swern oxidation / 5.2: Swern oxidation / 6.1: Mukaiyama reaction;
DOI:10.1021/jo101782q
