Technology Process of (3R,4R,5E)-6-iodo-4-methylhex-5-en-3-yl (2R,3S,4S,5R,6S,8R)-3,9-dihydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethylnonanoate
There total 12 articles about (3R,4R,5E)-6-iodo-4-methylhex-5-en-3-yl (2R,3S,4S,5R,6S,8R)-3,9-dihydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethylnonanoate which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
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1443051-51-1
(3R,4R,5E)-6-iodo-4-methylhex-5-en-3-yl (2R,3S,4S,5R,6S,8R)-3,9-dihydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethylnonanoate
- Guidance literature:
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With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
at 0 - 20 ℃;
for 6h;
stereoselective reaction;
DOI:10.1016/j.tetlet.2013.04.023
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1443051-51-1
(3R,4R,5E)-6-iodo-4-methylhex-5-en-3-yl (2R,3S,4S,5R,6S,8R)-3,9-dihydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethylnonanoate
- Guidance literature:
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Multi-step reaction with 5 steps
1: sodium tetrahydroborate / methanol / 3 h / 20 °C
2: Dess-Martin periodane / dichloromethane / 1 h
3: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / tert-butyl alcohol; water
4: 2,4,6-trichlorobenzoyl chloride; triethylamine; dmap / toluene / 2 h / 0 - 20 °C
5: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 - 20 °C
With
dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; Dess-Martin periodane; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol;
4: |Yamaguchi Lactonization;
DOI:10.1016/j.tetlet.2013.04.023
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1443051-51-1
(3R,4R,5E)-6-iodo-4-methylhex-5-en-3-yl (2R,3S,4S,5R,6S,8R)-3,9-dihydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethylnonanoate
- Guidance literature:
-
Multi-step reaction with 7 steps
1: titanium tetrachloride; (-)-sparteine / dichloromethane / 2 h / 0 °C
2: 2,6-dimethylpyridine / dichloromethane
3: sodium tetrahydroborate / methanol / 3 h / 20 °C
4: Dess-Martin periodane / dichloromethane / 1 h
5: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / tert-butyl alcohol; water
6: 2,4,6-trichlorobenzoyl chloride; triethylamine; dmap / toluene / 2 h / 0 - 20 °C
7: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 - 20 °C
With
2,6-dimethylpyridine; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; titanium tetrachloride; Dess-Martin periodane; triethylamine; (-)-sparteine;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol;
6: |Yamaguchi Lactonization;
DOI:10.1016/j.tetlet.2013.04.023
