Technology Process of (2R,3S)-3-Hydroxy-2-(3-hydroxy-propyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester
There total 13 articles about (2R,3S)-3-Hydroxy-2-(3-hydroxy-propyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 13 steps
1: 90 percent / NaBH4; CeCl3 / methanol / 0 °C
2: H2 / PtO2
3: Et3N
4: NaN3 / dimethylformamide / Heating
5: LiAlH4 / tetrahydrofuran
6: K2CO3
7: 90 percent / NaH / dimethylformamide
8: TBAF / tetrahydrofuran
9: Et3N
10: LiI / tetrahydrofuran
11: Zn; AcOH / ethanol
12: 94 percent / NaBH4 / ethanol
13: bis(tricyclohexylphosphine)benzylideneruthenium(IV)dichlorid
With
sodium tetrahydroborate; lithium aluminium tetrahydride; Grubbs catalyst first generation; sodium azide; cerium(III) chloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; potassium carbonate; acetic acid; triethylamine; lithium iodide; zinc;
platinum(IV) oxide;
In
tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;
1: Reduction / 2: Catalytic hydrogenation / 3: Substitution / 4: Substitution / 5: Reduction / 6: Substitution / 7: Substitution / 8: desilylation / 9: Substitution / 10: Substitution / 11: Reduction / 12: Reduction / 13: Cyclization;
DOI:10.1021/ol006384f
- Guidance literature:
-
Multi-step reaction with 12 steps
1: H2 / PtO2
2: Et3N
3: NaN3 / dimethylformamide / Heating
4: LiAlH4 / tetrahydrofuran
5: K2CO3
6: 90 percent / NaH / dimethylformamide
7: TBAF / tetrahydrofuran
8: Et3N
9: LiI / tetrahydrofuran
10: Zn; AcOH / ethanol
11: 94 percent / NaBH4 / ethanol
12: bis(tricyclohexylphosphine)benzylideneruthenium(IV)dichlorid
With
sodium tetrahydroborate; lithium aluminium tetrahydride; Grubbs catalyst first generation; sodium azide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; potassium carbonate; acetic acid; triethylamine; lithium iodide; zinc;
platinum(IV) oxide;
In
tetrahydrofuran; ethanol; N,N-dimethyl-formamide;
1: Catalytic hydrogenation / 2: Substitution / 3: Substitution / 4: Reduction / 5: Substitution / 6: Substitution / 7: desilylation / 8: Substitution / 9: Substitution / 10: Reduction / 11: Reduction / 12: Cyclization;
DOI:10.1021/ol006384f
- Guidance literature:
-
Multi-step reaction with 11 steps
1: Et3N
2: NaN3 / dimethylformamide / Heating
3: LiAlH4 / tetrahydrofuran
4: K2CO3
5: 90 percent / NaH / dimethylformamide
6: TBAF / tetrahydrofuran
7: Et3N
8: LiI / tetrahydrofuran
9: Zn; AcOH / ethanol
10: 94 percent / NaBH4 / ethanol
11: bis(tricyclohexylphosphine)benzylideneruthenium(IV)dichlorid
With
sodium tetrahydroborate; lithium aluminium tetrahydride; Grubbs catalyst first generation; sodium azide; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; acetic acid; triethylamine; lithium iodide; zinc;
In
tetrahydrofuran; ethanol; N,N-dimethyl-formamide;
1: Substitution / 2: Substitution / 3: Reduction / 4: Substitution / 5: Substitution / 6: desilylation / 7: Substitution / 8: Substitution / 9: Reduction / 10: Reduction / 11: Cyclization;
DOI:10.1021/ol006384f
![(1S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one](/Databaselist/images/loading.webp)
