Technology Process of Acetic acid (E)-(4R,5R)-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-7-oxo-hept-2-enyl ester
There total 10 articles about Acetic acid (E)-(4R,5R)-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-7-oxo-hept-2-enyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1: (dihydroquinidine)2-phthalazine; potassium osmate; aq. potassium ferricyanide / K2CO3 / 2-methyl-propan-2-ol / 12 h / 20 °C
2: BF3*Et2O / CH2Cl2 / 0.5 h / 0 °C
3: 1.33 g / LiAlH4 / diethyl ether / 1 h / 20 °C
4: DMSO; oxalyl chloride; Et3N / CH2Cl2 / -78 - 20 °C
5: 546 mg / CH2Cl2 / 4 h / Heating
6: DIBAL / diethyl ether / 12 h / -78 - 20 °C
7: 1.18 g / Et3N; DMAP / CH2Cl2 / 3 h / 20 °C
8: TBAF / tetrahydrofuran / 24 h / 20 °C
9: 3.76 g / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
With
dmap; potassium osmate(VI); lithium aluminium tetrahydride; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; potassium hexacyanoferrate(III);
potassium carbonate;
In
tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl alcohol;
1: Sharpless asymmetric dihydroxylation / 4: Swern oxidation / 5: Wittig olefination;
DOI:10.1002/chem.200500892
- Guidance literature:
-
Multi-step reaction with 8 steps
1: BF3*Et2O / CH2Cl2 / 0.5 h / 0 °C
2: 1.33 g / LiAlH4 / diethyl ether / 1 h / 20 °C
3: DMSO; oxalyl chloride; Et3N / CH2Cl2 / -78 - 20 °C
4: 546 mg / CH2Cl2 / 4 h / Heating
5: DIBAL / diethyl ether / 12 h / -78 - 20 °C
6: 1.18 g / Et3N; DMAP / CH2Cl2 / 3 h / 20 °C
7: TBAF / tetrahydrofuran / 24 h / 20 °C
8: 3.76 g / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
With
dmap; lithium aluminium tetrahydride; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane;
3: Swern oxidation / 4: Wittig olefination;
DOI:10.1002/chem.200500892
