Technology Process of (2R,3S,4S,5S)-1-tosyl-3,4,5-triacetoxy-2-phenylmethoxymethyl piperidine
There total 12 articles about (2R,3S,4S,5S)-1-tosyl-3,4,5-triacetoxy-2-phenylmethoxymethyl piperidine which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: K3Fe(CN)6; (DHQD)2-PHAL; K2OsO2(OH)4 / 2-methyl-propan-2-ol / 4 h / 0 °C
2.1: KOH / 2 h / 60 °C
3.1: aq. NaN3 / dimethylformamide / 12 h / 120 °C
4.1: NaH / dimethylformamide / 2 h / 0 °C
5.1: LiAlH4 / tetrahydrofuran / 4 h / Heating
5.2: pyridine / 0.5 h / 0 °C
6.1: 82.4 percent / m-CPBA / CH2Cl2 / 20 °C
7.1: 90 percent / BF3*Et2O; 4A sieves / tetrahydrofuran / 4 h / 0 °C
8.1: 97.4 percent / CeCl3; NaBH4 / methanol / 2 h / -30 °C
9.1: 86 percent / triethylamine; DMAP / CH2Cl2 / 2 h / 0 °C
10.1: 86 percent / aq. formic acid; NaBH4 / 4 h / 0 °C
11.1: 93 percent / K3Fe(CN)6; (DHQD)2-PHAL; K2OsO2(OH)4 / 2-methyl-propan-2-ol / 4 h / 0 °C
12.1: 71 percent / triethylamine; DMAP / CH2Cl2 / 2 h / 0 °C
With
dmap; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; formic acid; sodium azide; cerium(III) chloride; potassium dioxotetrahydroxoosmate(VI); 4 A molecular sieve; boron trifluoride diethyl etherate; sodium hydride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; 3-chloro-benzenecarboperoxoic acid; potassium hexacyanoferrate(III);
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
1.1: Oxidation / 2.1: Carboxylation / 3.1: Decomposition / 4.1: Alkylation / 5.1: Reduction / 5.2: Tosylation / 6.1: Oxidation / 7.1: Alkylation / 8.1: Reduction / 9.1: Acetylation / 10.1: Reduction / 11.1: Oxidation / 12.1: Acetylation;
DOI:10.1016/S0957-4166(99)00382-1
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: KOH / 2 h / 60 °C
2.1: aq. NaN3 / dimethylformamide / 12 h / 120 °C
3.1: NaH / dimethylformamide / 2 h / 0 °C
4.1: LiAlH4 / tetrahydrofuran / 4 h / Heating
4.2: pyridine / 0.5 h / 0 °C
5.1: 82.4 percent / m-CPBA / CH2Cl2 / 20 °C
6.1: 90 percent / BF3*Et2O; 4A sieves / tetrahydrofuran / 4 h / 0 °C
7.1: 97.4 percent / CeCl3; NaBH4 / methanol / 2 h / -30 °C
8.1: 86 percent / triethylamine; DMAP / CH2Cl2 / 2 h / 0 °C
9.1: 86 percent / aq. formic acid; NaBH4 / 4 h / 0 °C
10.1: 93 percent / K3Fe(CN)6; (DHQD)2-PHAL; K2OsO2(OH)4 / 2-methyl-propan-2-ol / 4 h / 0 °C
11.1: 71 percent / triethylamine; DMAP / CH2Cl2 / 2 h / 0 °C
With
dmap; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; formic acid; sodium azide; cerium(III) chloride; potassium dioxotetrahydroxoosmate(VI); 4 A molecular sieve; boron trifluoride diethyl etherate; sodium hydride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; 3-chloro-benzenecarboperoxoic acid; potassium hexacyanoferrate(III);
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
1.1: Carboxylation / 2.1: Decomposition / 3.1: Alkylation / 4.1: Reduction / 4.2: Tosylation / 5.1: Oxidation / 6.1: Alkylation / 7.1: Reduction / 8.1: Acetylation / 9.1: Reduction / 10.1: Oxidation / 11.1: Acetylation;
DOI:10.1016/S0957-4166(99)00382-1