Technology Process of methyl (Z)--((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-6,6-dichlorohex-2-enoate
There total 15 articles about methyl (Z)--((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-6,6-dichlorohex-2-enoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate;
With
18-crown-6 ether; potassium hexamethylsilazane;
In
tetrahydrofuran; toluene;
at -78 ℃;
for 0.166667h;
Inert atmosphere;
4-((4R,5S,6S)-6-(benzyloxymethyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-4,4-dichlorobutanal;
In
tetrahydrofuran; toluene;
at -78 ℃;
for 0.25h;
Inert atmosphere;
DOI:10.1021/jacs.9b05013
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: sodium tetrahydroborate / methanol / 1.33 h / -78 °C / Inert atmosphere
1.2: 0.17 h / -78 - 20 °C / Inert atmosphere
2.1: pyridinium p-toluenesulfonate / dichloromethane / 24.67 h / 0 - 20 °C / Inert atmosphere
3.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere
4.1: Dess-Martin periodane / dichloromethane / 1.08 h / 0 - 20 °C / Inert atmosphere
5.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
5.2: 0.25 h / -78 °C / Inert atmosphere
With
sodium tetrahydroborate; 18-crown-6 ether; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; Dess-Martin periodane; acetic acid;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
4.1: Dess-Martin oxidation / 5.1: Still-Gennari olefination / 5.2: Still-Gennari olefination;
DOI:10.1002/anie.201102521
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: zirconium(IV) chloride / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
1.2: 0.08 h / 0 - 20 °C / Inert atmosphere
2.1: sodium tetrahydroborate / methanol / 1.33 h / -78 °C / Inert atmosphere
2.2: 0.17 h / -78 - 20 °C / Inert atmosphere
3.1: pyridinium p-toluenesulfonate / dichloromethane / 24.67 h / 0 - 20 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere
5.1: Dess-Martin periodane / dichloromethane / 1.08 h / 0 - 20 °C / Inert atmosphere
6.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
6.2: 0.25 h / -78 °C / Inert atmosphere
With
sodium tetrahydroborate; 18-crown-6 ether; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; zirconium(IV) chloride; potassium hexamethylsilazane; Dess-Martin periodane; acetic acid;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
5.1: Dess-Martin oxidation / 6.1: Still-Gennari olefination / 6.2: Still-Gennari olefination;
DOI:10.1002/anie.201102521
