Technology Process of (2S,5R,6S)-((S)-1-(benzyloxy)but-3-en-2-yl) 5-((2-methoxyethoxy)methoxy)-2,6-dimethyldec-9-enoate
There total 8 articles about (2S,5R,6S)-((S)-1-(benzyloxy)but-3-en-2-yl) 5-((2-methoxyethoxy)methoxy)-2,6-dimethyldec-9-enoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(2S,5R,6S)-5-((2-methoxyethoxy)methoxy)-2,6-dimethyldec-9-enoic acid;
With
2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran;
at 0 ℃;
for 1h;
(S)-1-(benzyloxy)but-3-en-2-ol;
With
dmap;
In
tetrahydrofuran;
at 20 ℃;
for 6h;
DOI:10.1016/j.tetasy.2012.07.006
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C
2.1: di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.17 h / 0 °C
2.2: 0.5 h / 0 °C
2.3: 1 h / 0 °C
3.1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C
4.1: dmap; triethylamine / dichloromethane / 20 h / 0 - 20 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Reflux
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
7.1: ammonia; lithium / tetrahydrofuran / 1 h / -78 °C
8.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C
9.1: 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 °C
9.2: 6 h / 20 °C
With
dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; di-n-butylboryl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; ammonia; lithium; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
2.1: |Evans Aldol Reaction / 2.2: |Evans Aldol Reaction / 7.1: |Birch Reduction;
DOI:10.1016/j.tetasy.2012.07.006
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.17 h / 0 °C
1.2: 0.5 h / 0 °C
1.3: 1 h / 0 °C
2.1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C
3.1: dmap; triethylamine / dichloromethane / 20 h / 0 - 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Reflux
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
6.1: ammonia; lithium / tetrahydrofuran / 1 h / -78 °C
7.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C
8.1: 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 °C
8.2: 6 h / 20 °C
With
dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; di-n-butylboryl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; ammonia; lithium; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
1.1: |Evans Aldol Reaction / 1.2: |Evans Aldol Reaction / 6.1: |Birch Reduction;
DOI:10.1016/j.tetasy.2012.07.006
