(1'S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-(2',2'-bisthioethyl-1'-hydroxy)ethyl piperidine

Base Information

Chemical Name:(1'S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-(2',2'-bisthioethyl-1'-hydroxy)ethyl piperidine
CAS No.:123130-05-2
Molecular Formula:C₁₉H₂₉NO₄S₂
Molecular Weight:399.576
Hs Code.:

Synonyms:(1'S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-(2',2'-bisthioethyl-1'-hydroxy)ethyl piperidine

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

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

There total 16 articles about (1'S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-(2',2'-bisthioethyl-1'-hydroxy)ethyl 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: 89.0%

: 123165-55-9
(1S,3S,7S,8S)-N-benzyloxycarbonyl-5,5-dimethyl-11-aza-2,4,6-trioxatricyclo<6.4.0.0^3,7>dodecane

: 75-08-1
ethanethiol

: 123130-05-2
(1'S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-(2',2'-bisthioethyl-1'-hydroxy)ethyl piperidine

Guidance literature:: With trifluoroacetic acid;
DOI:10.1039/P19890001065

Reference yield:

: 172751-32-5
5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose

: 123130-05-2
(1'S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-(2',2'-bisthioethyl-1'-hydroxy)ethyl piperidine

Guidance literature:: Multi-step reaction with 11 steps

1: benzene / 4 h / Heating

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

3: 88 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

4: 98 percent / pyridine / 3 h / 0 °C

5: 96 percent / NaN₃ / dimethylformamide / 6 h / 50 °C

6: 95 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

7: 94 percent / pyridine / 3 h / 0 °C

8: H₂ / Pd black / ethanol / Ambient temperature

9: NaOAc / ethanol / 10 h / Heating

10: aq. NaHCO₃ / ethyl acetate / 0 °C

11: 89 percent / H₂O; trifluoroacetic acid / 4 h / 0 °C

With lithium aluminium tetrahydride; sodium azide; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; sodium hydrogencarbonate; palladium on activated charcoal; palladium; In tetrahydrofuran; pyridine; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; trifluoroacetic acid; benzene;
DOI:10.1016/0040-4020(94)01009-O

Reference yield:

: 114738-04-4
(3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

: 123130-05-2
(1'S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-(2',2'-bisthioethyl-1'-hydroxy)ethyl piperidine

Guidance literature:: Multi-step reaction with 12 steps

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

2: benzene / 4 h / Heating

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

4: 88 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

5: 98 percent / pyridine / 3 h / 0 °C

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

7: 95 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

8: 94 percent / pyridine / 3 h / 0 °C

9: H₂ / Pd black / ethanol / Ambient temperature

10: NaOAc / ethanol / 10 h / Heating

11: aq. NaHCO₃ / ethyl acetate / 0 °C

12: 89 percent / H₂O; trifluoroacetic acid / 4 h / 0 °C

With lithium aluminium tetrahydride; sodium azide; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; pyridinium perchlorate; sodium hydrogencarbonate; palladium on activated charcoal; palladium; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; trifluoroacetic acid; benzene;
DOI:10.1016/0040-4020(94)01009-O