Technology Process of (4R,5S)-4-[(E)-(1R,2R,3S)-7-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3,5-trimethyl-hept-5-enyl]-2,2-dimethyl-[1,3]dioxane-5-carbaldehyde
There total 22 articles about (4R,5S)-4-[(E)-(1R,2R,3S)-7-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3,5-trimethyl-hept-5-enyl]-2,2-dimethyl-[1,3]dioxane-5-carbaldehyde which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
Dess-Martin periodane;
In
dichloromethane;
at 20 ℃;
for 1.5h;
DOI:10.1021/ol049219z
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 68 percent / PdCl2[P(o-Tol)3]2 / tetrahydrofuran / 96 h / 20 °C
2.1: 96 percent / DIBAL / CH2Cl2; hexane / -78 - 45 °C
3.1: 100 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
4.1: Sn(OTf)2; Et3N / CH2Cl2 / 3 h / -78 °C
4.2: 77 percent / CH2Cl2 / 6 h / -78 °C
5.1: diethylmethoxyborane / tetrahydrofuran; methanol / 0.25 h / 20 °C
5.2: 73 percent / NaBH4 / tetrahydrofuran; methanol / 48 h / -78 °C
6.1: 92 percent / TBAF / tetrahydrofuran / 4 h / 20 °C
7.1: 86 percent / PPTS / CH2Cl2 / 0.5 h / 20 °C
8.1: 94 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C
9.1: 68 percent / DDQ / CH2Cl2; aq. phosphate buffer / 6 h / 0 °C / pH 7
10.1: 67.4 mg / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 20 °C
With
2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; diethyl methoxy borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
dichlorobis(tri-O-tolylphosphine)palladium;
In
tetrahydrofuran; methanol; phosphate buffer; hexane; dichloromethane;
4.2: Paterson's stereoselective aldol reaction;
DOI:10.1021/ol049219z
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 80 percent / Sn(OTf)2; triethylamine
2: Et2BOMe; NaBH4
3: TBAF / tetrahydrofuran
4: PPTS
5: 2,6-lutidine
6: 65 percent / DDQ
With
2,6-dimethylpyridine; sodium tetrahydroborate; tin(II) trifluoromethanesulfonate; diethyl methoxy borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran;
1: Swern oxidation / 8: Swern oxidation;
DOI:10.1016/j.tetlet.2005.07.029
![{(4S,5S)-4-[(E)-(1R,2R,3S)-7-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3,5-trimethyl-hept-5-enyl]-2,2-dimethyl-[1,3]dioxan-5-yl}-methanol](/Databaselist/images/loading.webp)
