(S)-1-((3S,4S,5S)-1-benzyl-4-fluoro-5-hydroxypiperidin-3-yl)ethane-1,2-diol

Base Information

Chemical Name:(S)-1-((3S,4S,5S)-1-benzyl-4-fluoro-5-hydroxypiperidin-3-yl)ethane-1,2-diol
CAS No.:1332850-57-3
Molecular Formula:C₁₄H₂₀FNO₃
Molecular Weight:269.316
Hs Code.:

Synonyms:(S)-1-((3S,4S,5S)-1-benzyl-4-fluoro-5-hydroxypiperidin-3-yl)ethane-1,2-diol

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Chemical Property of (S)-1-((3S,4S,5S)-1-benzyl-4-fluoro-5-hydroxypiperidin-3-yl)ethane-1,2-diol

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Technology Process of (S)-1-((3S,4S,5S)-1-benzyl-4-fluoro-5-hydroxypiperidin-3-yl)ethane-1,2-diol

There total 8 articles about (S)-1-((3S,4S,5S)-1-benzyl-4-fluoro-5-hydroxypiperidin-3-yl)ethane-1,2-diol 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: 90.0%

: 1332850-55-1
(3S,4S,5S)-1-benzyl-3-(benzyloxy)-5-((S)-1,2-bis(benzyloxy)ethyl)-4-fluoropiperidine

: 1332850-57-3
(S)-1-((3S,4S,5S)-1-benzyl-4-fluoro-5-hydroxypiperidin-3-yl)ethane-1,2-diol

Guidance literature:: (3S,4S,5S)-1-benzyl-3-(benzyloxy)-5-((S)-1,2-bis(benzyloxy)ethyl)-4-fluoropiperidine; With boron trichloride; In dichloromethane; at 0 ℃; for 3h; Inert atmosphere;

With methanol; In dichloromethane; Inert atmosphere;
DOI:10.1016/j.jfluchem.2011.05.031

Reference yield:

: 1309594-26-0
(5S,6S,E)-6-((S)-1,2-bis(benzyloxy)ethyl)-5-fluoroocta-2,7-dien-4-one

: 1332850-57-3
(S)-1-((3S,4S,5S)-1-benzyl-4-fluoro-5-hydroxypiperidin-3-yl)ethane-1,2-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.33 h / 0 °C

2.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

3.1: ozone / methanol; dichloromethane / -78 °C

3.2: 3 h / 20 °C

4.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

5.1: 18 h / 80 °C

6.1: boron trichloride / dichloromethane / 3 h / 0 °C / Inert atmosphere

6.2: Inert atmosphere

With dmap; sodium tetrahydroborate; cerium(III) chloride heptahydrate; boron trichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; mineral oil;
DOI:10.1016/j.jfluchem.2011.05.031

Reference yield:

: 1332850-49-3
(4S,5S,6S,E)-6-((S)-1,2-bis(benzyloxy)ethyl)-5-fluoroocta-2,7-dien-4-ol

: 1332850-57-3
(S)-1-((3S,4S,5S)-1-benzyl-4-fluoro-5-hydroxypiperidin-3-yl)ethane-1,2-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: ozone / methanol; dichloromethane / -78 °C

2.2: 3 h / 20 °C

3.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

4.1: 18 h / 80 °C

5.1: boron trichloride / dichloromethane / 3 h / 0 °C / Inert atmosphere

5.2: Inert atmosphere

With dmap; boron trichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; mineral oil;
DOI:10.1016/j.jfluchem.2011.05.031