Technology Process of (3aR,4aS,5S,8aS,8bR)-5-(benzyloxy)-8a-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-7(4aH)-one
There total 12 articles about (3aR,4aS,5S,8aS,8bR)-5-(benzyloxy)-8a-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-7(4aH)-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
L-proline;
In
N,N-dimethyl-formamide;
at 20 ℃;
for 72h;
DOI:10.1021/jo401166q
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: magnesium bromide diethyl etherate / dichloromethane / 0.08 h / -78 °C
1.2: 3 h / 78 °C
2.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C
3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 6 h / 23 °C
4.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 6 h / 0 - 23 °C / Molecular sieve
5.1: palladium dichloride; copper diacetate; oxygen / water; N,N-dimethyl acetamide / 48 h
6.1: L-proline / N,N-dimethyl-formamide / 72 h / 20 °C
With
magnesium bromide diethyl etherate; water; oxygen; copper diacetate; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; L-proline; palladium dichloride;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; mineral oil;
1.1: |Sakurai Allylation / 1.2: |Sakurai Allylation;
DOI:10.1021/jo401166q
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: copper(II) sulfate; sulfuric acid / 1 h / 23 °C
2.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 2 h / 0 - 23 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 23 °C
4.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide; dichloromethane / 0.17 h / -20 °C
5.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C
5.2: 3 h / -78 °C
6.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C
7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 6 h / 23 °C
8.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 6 h / 0 - 23 °C / Molecular sieve
9.1: palladium dichloride; copper diacetate; oxygen / water; N,N-dimethyl acetamide / 48 h
10.1: L-proline / N,N-dimethyl-formamide / 72 h / 20 °C
With
sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; oxygen; copper diacetate; sodium acetate; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; sodium hydride; copper(II) sulfate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; L-proline; palladium dichloride;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil;
4.1: |Parikh-Doering Oxidation / 5.1: |Sakurai Allylation / 5.2: |Sakurai Allylation;
DOI:10.1021/jo401166q
