Technology Process of (3S,4S,5R,6S,7S,8E,10E)-3,4-bis(tert-butyldimethylsilyloxy)-5,7-dihydroxy-6,8,10-trimethyldodeca-8,10-dienyl benzoate
There total 14 articles about (3S,4S,5R,6S,7S,8E,10E)-3,4-bis(tert-butyldimethylsilyloxy)-5,7-dihydroxy-6,8,10-trimethyldodeca-8,10-dienyl benzoate 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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1103963-58-1
(3S,4S,5R,6S,7S,8E,10E)-3,4-bis(tert-butyldimethylsilyloxy)-5,7-dihydroxy-6,8,10-trimethyldodeca-8,10-dienyl benzoate
- Guidance literature:
-
With
sodium tetrahydroborate; diethyl methoxy borane;
In
tetrahydrofuran; methanol;
at -30 ℃;
for 3h;
Inert atmosphere;
DOI:10.1002/chem.201304297
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-
1103963-58-1
(3S,4S,5R,6S,7S,8E,10E)-3,4-bis(tert-butyldimethylsilyloxy)-5,7-dihydroxy-6,8,10-trimethyldodeca-8,10-dienyl benzoate
- Guidance literature:
-
C34H58O6Si2;
With
diethyl methoxy borane;
In
tetrahydrofuran; methanol;
at -30 ℃;
With
sodium tetrahydroborate;
In
tetrahydrofuran; methanol;
at -15 ℃;
for 1h;
With
methanol; dihydrogen peroxide;
In
tetrahydrofuran;
at 20 ℃;
for 2.5h;
DOI:10.1002/anie.200803271
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-
1103963-58-1
(3S,4S,5R,6S,7S,8E,10E)-3,4-bis(tert-butyldimethylsilyloxy)-5,7-dihydroxy-6,8,10-trimethyldodeca-8,10-dienyl benzoate
- Guidance literature:
-
Multi-step reaction with 8 steps
1: sodium dihydrogenphosphate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 40 °C / Inert atmosphere
2: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere
3: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
4: sodium periodate; rhodium(III) chloride hydrate / acetonitrile; water / 5 h / 20 °C / Inert atmosphere
5: (1S)-10-camphorsulfonic acid / ethanol / 27 h / 0 °C / Inert atmosphere
6: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere
7: boron trifluoride diethyl etherate / dichloromethane / 2.5 h / -40 °C / Inert atmosphere
8: diethyl methoxy borane; sodium tetrahydroborate / methanol; tetrahydrofuran / 3 h / -30 °C / Inert atmosphere
With
2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; rhodium(III) chloride hydrate; diethyl methoxy borane; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; acetonitrile;
1: |Baeyer-Villiger Ketone Oxidation / 7: |Mukaiyama Aldol Addition;
DOI:10.1002/chem.201304297
