(3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-((S)-1,2-dihydroxyethyl)piperidine

Base Information

Chemical Name:(3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-((S)-1,2-dihydroxyethyl)piperidine
CAS No.:162517-95-5
Molecular Formula:C₁₅H₂₁NO₅
Molecular Weight:295.335
Hs Code.:

Synonyms:(3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-((S)-1,2-dihydroxyethyl)piperidine

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Chemical Property of (3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-((S)-1,2-dihydroxyethyl)piperidine

Chemical Property:

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Technology Process of (3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-((S)-1,2-dihydroxyethyl)piperidine

There total 15 articles about (3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-((S)-1,2-dihydroxyethyl)piperidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 1941-50-0
D-arabinose diethyl dithioacetal

: 162517-95-5
(3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-((S)-1,2-dihydroxyethyl)piperidine

Guidance literature:: Multi-step reaction with 14 steps

1: 95 percent / imidazole / dimethylformamide / 0 °C

2: 1.) HgO, HgCl₂; 2.) CuSO₄, dl-camphorsulfonic acid / 1.) aq. acetone, 6 h; 2.) acetone, RT, 4 h

3: pyridinium perchlorate, 3A molecular sieve / CH₂Cl₂ / 4 h / Ambient temperature

4: benzene / 4 h / Heating

5: H₂ / 10percent Pd/C / ethyl acetate / 48 h / Ambient temperature

6: 88 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

7: 98 percent / pyridine / 3 h / 0 °C

8: 96 percent / NaN₃ / dimethylformamide / 6 h / 50 °C

9: 95 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

10: 94 percent / pyridine / 3 h / 0 °C

11: H₂ / Pd black / ethanol / Ambient temperature

12: NaOAc / ethanol / 10 h / Heating

13: aq. NaHCO₃ / ethyl acetate / 0 °C

14: 2.) NaBH₄ / 1.) 80percent aq. AcOH, 50 deg C, 12 h; 2.) EtOH

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; 3 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; pyridinium perchlorate; sodium hydrogencarbonate; copper(II) sulfate; mercury dichloride; mercury(II) oxide; palladium on activated charcoal; palladium; In tetrahydrofuran; pyridine; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1016/0040-4020(94)01009-O

Reference yield:

: 123107-59-5
3-C-(2'-azidoethyl)-5-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-isopropylidene-β-D-lyxofuranose

: 162517-95-5
(3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-((S)-1,2-dihydroxyethyl)piperidine

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

2: 94 percent / pyridine / 3 h / 0 °C

3: H₂ / Pd black / ethanol / Ambient temperature

4: NaOAc / ethanol / 10 h / Heating

5: aq. NaHCO₃ / ethyl acetate / 0 °C

6: 2.) NaBH₄ / 1.) 80percent aq. AcOH, 50 deg C, 12 h; 2.) EtOH

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; sodium hydrogencarbonate; palladium; In tetrahydrofuran; pyridine; ethanol; ethyl acetate;
DOI:10.1016/0040-4020(94)01009-O

Reference yield:

: 162517-92-2
5-O-(tert-butyldiphenylsilyl)-3-C-(2'-hydroxyethyl)-3-deoxy-1,2-O-isopropylidene-β-D-lyxofuranose

: 162517-95-5
(3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-((S)-1,2-dihydroxyethyl)piperidine

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / pyridine / 3 h / 0 °C

2: 96 percent / NaN₃ / dimethylformamide / 6 h / 50 °C

3: 95 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

4: 94 percent / pyridine / 3 h / 0 °C

5: H₂ / Pd black / ethanol / Ambient temperature

6: NaOAc / ethanol / 10 h / Heating

7: aq. NaHCO₃ / ethyl acetate / 0 °C

8: 2.) NaBH₄ / 1.) 80percent aq. AcOH, 50 deg C, 12 h; 2.) EtOH

With sodium tetrahydroborate; sodium azide; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; sodium hydrogencarbonate; palladium; In tetrahydrofuran; pyridine; ethanol; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(94)01009-O