Technology Process of (-)-(5S,6S)-1-allyl-5-benzyloxy-6-[(E)-(t-butyldiphenylsilyloxy)-1-propenyl]-1,2,5,6-tetrahydro-2-pyridinone
There total 10 articles about (-)-(5S,6S)-1-allyl-5-benzyloxy-6-[(E)-(t-butyldiphenylsilyloxy)-1-propenyl]-1,2,5,6-tetrahydro-2-pyridinone which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(+)-(5S,6S)-5-benzyloxy-6-[(E)-(t-butyldiphenylsilyloxy)-1-propenyl]-1,2,5,6-tetrahydro-2-pyridinone;
With
sodium hydride;
In
tetrahydrofuran;
at 0 ℃;
for 0.333333h;
allyl bromide;
With
tetra-(n-butyl)ammonium iodide;
In
tetrahydrofuran;
at 20 ℃;
for 1h;
DOI:10.1021/jo026817n
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: benzene / 24 h / Heating
2.1: 7.39 g / NaBH4 / tetrahydrofuran; H2O / 2 h / 20 °C
3.1: DMAP; imidazole / dimethylformamide / 24 h / 20 °C
4.1: 61 percent / (NH4)2Ce(NO3)6 / H2O; acetonitrile / 0.5 h / 0 °C
5.1: 97 percent / DMAP / acetonitrile / 0.17 h
6.1: 97 percent / LiAlH4 / tetrahydrofuran / 0.33 h / 0 °C
7.1: 2-iodoxybenzoic acid / dimethylsulfoxide / 5 h / 20 °C
8.1: methanol / 18 h / 20 °C
9.1: 2,6-lutidine; TMSOTf / CH2Cl2 / 1 h / 20 °C
9.2: 95 percent / DMAP / toluene / 1 h / Heating
10.1: NaH / tetrahydrofuran / 0.33 h / 0 °C
10.2: 88 percent / n-Bu4NI / tetrahydrofuran / 1 h / 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; sodium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jo026817n
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 7.39 g / NaBH4 / tetrahydrofuran; H2O / 2 h / 20 °C
2.1: DMAP; imidazole / dimethylformamide / 24 h / 20 °C
3.1: 61 percent / (NH4)2Ce(NO3)6 / H2O; acetonitrile / 0.5 h / 0 °C
4.1: 97 percent / DMAP / acetonitrile / 0.17 h
5.1: 97 percent / LiAlH4 / tetrahydrofuran / 0.33 h / 0 °C
6.1: 2-iodoxybenzoic acid / dimethylsulfoxide / 5 h / 20 °C
7.1: methanol / 18 h / 20 °C
8.1: 2,6-lutidine; TMSOTf / CH2Cl2 / 1 h / 20 °C
8.2: 95 percent / DMAP / toluene / 1 h / Heating
9.1: NaH / tetrahydrofuran / 0.33 h / 0 °C
9.2: 88 percent / n-Bu4NI / tetrahydrofuran / 1 h / 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; sodium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo026817n
