Technology Process of (3R,4R)-4-benzyloxy-2-formyl-6,7-methylenedioxy-3-triisopropylsilyloxymethyl-3,4-dihydronaphthalene
There total 13 articles about (3R,4R)-4-benzyloxy-2-formyl-6,7-methylenedioxy-3-triisopropylsilyloxymethyl-3,4-dihydronaphthalene which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
sodium hydride;
In
N,N-dimethyl-formamide;
at -10 - 20 ℃;
DOI:10.1021/jo991582+
- Guidance literature:
-
Multi-step reaction with 12 steps
1: 61 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C
2: 83 percent / NaBH4 / ethanol / 20 °C
3: 90 percent / acetic acid / 2 h / 80 °C
4: 99 percent / H2 / 10percent Pd/C / ethyl acetate / 6 h / 2482.38 Torr
5: 82 percent / LiAlH4 / diethyl ether / 24 h / Heating
6: 100 percent / DMAP / pyridine / 16 h / 20 °C
7: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8
8: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C
9: 100 percent / K2CO3 / methanol / 1.5 h / 20 °C
10: 100 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - -40 °C
11: 90 percent / NaOMe / methanol / 20 °C
12: 100 percent / NaH / dimethylformamide / -10 - 20 °C
With
1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; hydrogen; sodium methylate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine;
10percent Pd/C;
In
tetrahydrofuran; pyridine; methanol; phosphate buffer; diethyl ether; ethanol; hexane; dichloromethane; acetic acid; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;
1: Formylation / 2: Reduction / 3: Cycloaddition / 4: Catalytic hydrogenation / 5: Reduction / 6: Acetylation / 7: Deacetylation / 8: silylation / 9: Deacetylation / 10: Oxidation / 11: Ring cleavage / 12: Alkylation;
DOI:10.1021/jo991582+
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 83 percent / NaBH4 / ethanol / 20 °C
2: 90 percent / acetic acid / 2 h / 80 °C
3: 99 percent / H2 / 10percent Pd/C / ethyl acetate / 6 h / 2482.38 Torr
4: 82 percent / LiAlH4 / diethyl ether / 24 h / Heating
5: 100 percent / DMAP / pyridine / 16 h / 20 °C
6: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8
7: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C
8: 100 percent / K2CO3 / methanol / 1.5 h / 20 °C
9: 100 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - -40 °C
10: 90 percent / NaOMe / methanol / 20 °C
11: 100 percent / NaH / dimethylformamide / -10 - 20 °C
With
1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; sodium methylate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine;
10percent Pd/C;
In
pyridine; methanol; phosphate buffer; diethyl ether; ethanol; dichloromethane; acetic acid; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;
1: Reduction / 2: Cycloaddition / 3: Catalytic hydrogenation / 4: Reduction / 5: Acetylation / 6: Deacetylation / 7: silylation / 8: Deacetylation / 9: Oxidation / 10: Ring cleavage / 11: Alkylation;
DOI:10.1021/jo991582+
