Technology Process of (R)-3-Benzyloxy-tetradecanoic acid (4aR,6R,7R,8R,8aS)-7-((R)-3-benzyloxy-tetradecanoylamino)-6-(bis-benzyloxy-phosphoryloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
There total 6 articles about (R)-3-Benzyloxy-tetradecanoic acid (4aR,6R,7R,8R,8aS)-7-((R)-3-benzyloxy-tetradecanoylamino)-6-(bis-benzyloxy-phosphoryloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
n-butyllithium;
In
tetrahydrofuran; hexane;
at -50 ℃;
for 0.0833333h;
DOI:10.1248/cpb.35.1383
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 94 percent / ammonia / methanol; H2O / 12 h / Ambient temperature
2: 76 percent / p-toluenesulfonic acid / dimethylformamide / 2 h / Ambient temperature
3: 2.) sodium hydroxide / 1.) pyridine, 90 degC, 2 h; 2.) water, methanol, room t., 1.5 h
4: 80 percent / dicyclohexylcarbodiimide, 4-dimethylaminopyridine / CH2Cl2 / 5 h, 0 degC, room t., 12 h
5: 2.) iodine, pyridine / 1.) bis-(methyldiphenylphosphine)cycloocta-1,5-diene iridium (I) hexafluorophosphate / 1.) THF, 50 degC, 2 h; 2.) room t., 15 min, THF-water
6: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -50 °C
With
pyridine; dmap; sodium hydroxide; n-butyllithium; ammonia; iodine; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide;
(bis(diphenylphosphino)ethylene)(1,5-cyclooctadiene)iridium(I) hexafluorophosphate;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1248/cpb.35.1383
- Guidance literature:
-
Multi-step reaction with 3 steps
1: 80 percent / dicyclohexylcarbodiimide, 4-dimethylaminopyridine / CH2Cl2 / 5 h, 0 degC, room t., 12 h
2: 2.) iodine, pyridine / 1.) bis-(methyldiphenylphosphine)cycloocta-1,5-diene iridium (I) hexafluorophosphate / 1.) THF, 50 degC, 2 h; 2.) room t., 15 min, THF-water
3: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -50 °C
With
pyridine; dmap; n-butyllithium; iodine; dicyclohexyl-carbodiimide;
(bis(diphenylphosphino)ethylene)(1,5-cyclooctadiene)iridium(I) hexafluorophosphate;
In
tetrahydrofuran; hexane; dichloromethane;
DOI:10.1248/cpb.35.1383
