(2S,3S,5S)-2-benzyloxy-3-fluoro-5-hydroxymethyl-N-benzyloxypiperidine

Base Information

• Chemical Name: (2S,3S,5S)-2-benzyloxy-3-fluoro-5-hydroxymethyl-N-benzyloxypiperidine
• CAS No.: 151253-48-4
• Molecular Formula: C₂₀H₂₄FNO₃
• Molecular Weight: 345.414
• Mol file: 151253-48-4.mol

Synonyms:

Chemical Property of (2S,3S,5S)-2-benzyloxy-3-fluoro-5-hydroxymethyl-N-benzyloxypiperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5S)-2-benzyloxy-3-fluoro-5-hydroxymethyl-N-benzyloxypiperidine

There total 3 articles about (2S,3S,5S)-2-benzyloxy-3-fluoro-5-hydroxymethyl-N-benzyloxypiperidine 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:

(2S,3S)-2-Benzyloxy-3-fluoro-hex-5-enal O-benzyl-oxime → (2S,3S,5S)-2-benzyloxy-3-fluoro-5-hydroxymethyl-N-benzyloxypiperidine (151253-48-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / sodium cyanoborohydride, aq.HCl / methanol / 1 h / Ambient temperature; pH 3-4

2: 1.) mercury(II) trifluoroacetate; 2.) NaHCO₃, KCl; 3.) sodium borohydride, O₂ / 1.) THF, rt, 2 h; 2.) THF/water, rt, 2 h; 3.) perfluorotributylamine/hexafluoroisopropanol, rt, 10 min

With hydrogenchloride; sodium tetrahydroborate; potassium chloride; oxygen; mercury(II) trifluoroacetate; sodium cyanoborohydride; sodium hydrogencarbonate; In methanol;

DOI:10.1016/0040-4020(95)00859-7

Reference yield:

(2S,3S)-N-1-(2-benzyloxy-3-fluoro-5-hexenyl)-O-benzylhydroxylamine (151253-45-1) → (2S,3S,5S)-2-benzyloxy-3-fluoro-5-hydroxymethyl-N-benzyloxypiperidine (151253-48-4)

Guidance literature:

With sodium tetrahydroborate; potassium chloride; oxygen; mercury(II) trifluoroacetate; sodium hydrogencarbonate; Yield given. Multistep reaction; 1.) THF, rt, 2 h; 2.) THF/water, rt, 2 h; 3.) perfluorotributylamine/hexafluoroisopropanol, rt, 10 min;

DOI:10.1016/0040-4020(95)00859-7

Reference yield:

(2S,3S)-N-1-(2-benzyloxy-3-fluoro-5-hexenyl)-O-benzylhydroxylamine (151253-45-1) → (2S,3S,5S)-2-benzyloxy-3-fluoro-5-hydroxymethyl-N-benzyloxypiperidine (151253-48-4) + (2S,3S,5R)-2-benzyloxy-3-fluoro-5-hydroxymethyl-N-benzyloxypiperidine (151285-22-2)

Guidance literature:

With sodium tetrahydroborate; 1,1,1,3',3',3'-hexafluoro-propanol; potassium chloride; oxygen; mercury(II) trifluoroacetate; Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1039/c39930000984

upstream raw materials:

(2S,3S)-N-1-(2-benzyloxy-3-fluoro-5-hexenyl)-O-benzylhydroxylamine

Downstream raw materials:

1,3,4-trideoxy-3-fluoronojirimycin