(2R,4R,5R)-3-benzyloxymethyl-4-hydroxypiperidinium 5-sulfate

Base Information

• Chemical Name: (2R,4R,5R)-3-benzyloxymethyl-4-hydroxypiperidinium 5-sulfate
• CAS No.: 877463-70-2
• Molecular Formula: C₁₃H₁₉NO₆S
• Molecular Weight: 317.363
• Mol file: 877463-70-2.mol

Synonyms:(2R,4R,5R)-3-benzyloxymethyl-4-hydroxypiperidinium 5-sulfate

Chemical Property of (2R,4R,5R)-3-benzyloxymethyl-4-hydroxypiperidinium 5-sulfate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R,5R)-3-benzyloxymethyl-4-hydroxypiperidinium 5-sulfate

There total 5 articles about (2R,4R,5R)-3-benzyloxymethyl-4-hydroxypiperidinium 5-sulfate 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: 34.0%

(5R)-3-benzyloxymethyl-5-[(4R)-2,2-dioxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline (877463-68-8) → (2R,4R,5R)-3-benzyloxymethyl-4-hydroxypiperidinium 5-sulfate (877463-70-2)

Guidance literature:

With hydrogen; sodium carbonate; palladium on activated charcoal; In methanol; at 20 ℃; for 5h;

DOI:10.1021/jo0517388

Reference yield:

(5R)-3-benzyloxymethyl-5-[(4R)-2-oxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline (877463-66-6) → (2R,4R,5R)-3-benzyloxymethyl-4-hydroxypiperidinium 5-sulfate (877463-70-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.34 g / RuCl₃; NaIO₄ / acetonitrile; H₂O / 0.83 h / 20 °C

2: 34 percent / sodium carbonate; hydrogen / Pd/C / methanol / 5 h / 20 °C

With ruthenium trichloride; sodium periodate; hydrogen; sodium carbonate; palladium on activated charcoal; In methanol; water; acetonitrile;

DOI:10.1021/jo0517388

Reference yield:

(5R)-3-benzyloxymethyl-5-[(1R)-1,2-O-cyclohexylidene-1,2-dihydroxyethyl]-2-isoxazoline (877463-64-4) → (2R,4R,5R)-3-benzyloxymethyl-4-hydroxypiperidinium 5-sulfate (877463-70-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / acetic acid / H₂O / 80 °C

2: 85 percent / pyridine; SOCl₂ / CH₂Cl₂ / 2 h / 0 - 20 °C

3: 0.34 g / RuCl₃; NaIO₄ / acetonitrile; H₂O / 0.83 h / 20 °C

4: 34 percent / sodium carbonate; hydrogen / Pd/C / methanol / 5 h / 20 °C

With pyridine; ruthenium trichloride; sodium periodate; thionyl chloride; hydrogen; sodium carbonate; acetic acid; palladium on activated charcoal; In methanol; dichloromethane; water; acetonitrile;

DOI:10.1021/jo0517388

upstream raw materials:

(5R)-3-benzyloxymethyl-5-[(4R)-2,2-dioxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline

(5R)-3-benzyloxymethyl-5-[(4R)-2-oxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline

(5R)-3-benzyloxymethyl-5-[(1R)-1,2-O-cyclohexylidene-1,2-dihydroxyethyl]-2-isoxazoline

((2-nitroethoxy)methyl)benzene

Downstream raw materials:

(2R,3S)-1,3-O-benzylidene-1,3-dihydroxy-4-[(2R,4R,5R)-2-benzyloxymethyl-4,5-dihydroxypiperidinium-1-yl]butane-2-sulfate

(2S,3R)-1,3-dihydroxy-1,3-O-isopropylidene-4-[(2R,4R,5R)-2-benzyloxymethyl-4,5-dihydroxypiperidinium-1-yl]butane-2-sulfate

(2R,4R,5R)-3-benzyloxymethyl-4,5-dihydroxypiperidine