Technology Process of (2S,3S)-3-Allyloxycarbonylamino-2-benzoyloxymethyl-5-(2-methoxy-ethoxymethoxy)-2,3-dihydro-indole-1-carboxylic acid 2-trimethylsilanyl-ethyl ester
There total 14 articles about (2S,3S)-3-Allyloxycarbonylamino-2-benzoyloxymethyl-5-(2-methoxy-ethoxymethoxy)-2,3-dihydro-indole-1-carboxylic acid 2-trimethylsilanyl-ethyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
1.2: 94 percent / tetrahydrofuran / 6 h / 0 °C
2.1: 79 percent / NaOH; t-butyl hypochlorite; (DHQ)2PHAL / potassium osmate dihydrate / propan-1-ol; H2O / 2 h / 0 °C
3.1: 70 percent / LiBH4 / tetrahydrofuran / 0 - 20 °C
4.1: 88 percent / pyridine / CH2Cl2 / 2 h / -25 °C
5.1: 87 percent / DMAP / CH2Cl2 / 24 h / 20 °C
6.1: H2 / Lindlar catalyst / tetrahydrofuran / atmospheric pressure
7.1: 532 mg / K2CO3 / tetrahydrofuran / 24 h / 55 °C
8.1: 98 percent / pyridine / CH2Cl2 / 1 h / 0 °C
9.1: H2 / Pd/C / methanol / 3 h / atmospheric pressure
10.1: 617 mg / pyridine / tetrahydrofuran / 1 h / 0 °C
With
pyridine; dmap; sodium hydroxide; lithium borohydride; Hydroquinone 1,4-phthalazinediyl diether; tert-butylhypochlorite; hydrogen; sodium hydride; potassium carbonate;
potassium osmate(VI); palladium on activated charcoal; Lindlar's catalyst;
In
tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water;
2.1: Sharpless aminohydroxylation;
DOI:10.1002/anie.200462298
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 79 percent / NaOH; t-butyl hypochlorite; (DHQ)2PHAL / potassium osmate dihydrate / propan-1-ol; H2O / 2 h / 0 °C
2: 70 percent / LiBH4 / tetrahydrofuran / 0 - 20 °C
3: 88 percent / pyridine / CH2Cl2 / 2 h / -25 °C
4: 87 percent / DMAP / CH2Cl2 / 24 h / 20 °C
5: H2 / Lindlar catalyst / tetrahydrofuran / atmospheric pressure
6: 532 mg / K2CO3 / tetrahydrofuran / 24 h / 55 °C
7: 98 percent / pyridine / CH2Cl2 / 1 h / 0 °C
8: H2 / Pd/C / methanol / 3 h / atmospheric pressure
9: 617 mg / pyridine / tetrahydrofuran / 1 h / 0 °C
With
pyridine; dmap; sodium hydroxide; lithium borohydride; Hydroquinone 1,4-phthalazinediyl diether; tert-butylhypochlorite; hydrogen; potassium carbonate;
potassium osmate(VI); palladium on activated charcoal; Lindlar's catalyst;
In
tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water;
1: Sharpless aminohydroxylation;
DOI:10.1002/anie.200462298
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 88 percent / pyridine / CH2Cl2 / 2 h / -25 °C
2: 87 percent / DMAP / CH2Cl2 / 24 h / 20 °C
3: H2 / Lindlar catalyst / tetrahydrofuran / atmospheric pressure
4: 532 mg / K2CO3 / tetrahydrofuran / 24 h / 55 °C
5: 98 percent / pyridine / CH2Cl2 / 1 h / 0 °C
6: H2 / Pd/C / methanol / 3 h / atmospheric pressure
7: 617 mg / pyridine / tetrahydrofuran / 1 h / 0 °C
With
pyridine; dmap; hydrogen; potassium carbonate;
palladium on activated charcoal; Lindlar's catalyst;
In
tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/anie.200462298
