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

Base Information

• Chemical Name: (2R,3S)-1,3-O-benzylidene-1,3-dihydroxy-4-[(2R,4R,5R)-2-benzyloxymethyl-4,5-dihydroxypiperidinium-1-yl]butane-2-sulfate
• CAS No.: 877463-77-9
• Molecular Formula: C₂₄H₃₁NO₉S
• Molecular Weight: 509.577
• Mol file: 877463-77-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (2R,3S)-1,3-O-benzylidene-1,3-dihydroxy-4-[(2R,4R,5R)-2-benzyloxymethyl-4,5-dihydroxypiperidinium-1-yl]butane-2-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: 74.0%

(2R,4R,5R)-3-benzyloxymethyl-4,5-dihydroxypiperidine (877463-72-4) + 2,4-O-benzylidene-D-erythritol-1,3-cyclic-sulfate (302579-06-2) → (2R,3S)-1,3-O-benzylidene-1,3-dihydroxy-4-[(2R,4R,5R)-2-benzyloxymethyl-4,5-dihydroxypiperidinium-1-yl]butane-2-sulfate (877463-77-9)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; for 24h; Heating;

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,3S)-1,3-O-benzylidene-1,3-dihydroxy-4-[(2R,4R,5R)-2-benzyloxymethyl-4,5-dihydroxypiperidinium-1-yl]butane-2-sulfate (877463-77-9)

Guidance literature:

Multi-step reaction with 4 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

3: 86 percent / H₂SO₄ / dioxane; H₂O / 36 h / 50 °C

4: 74 percent / anhydrous sodium carbonate / tetrahydrofuran / 24 h / Heating

With ruthenium trichloride; sodium periodate; sulfuric acid; hydrogen; sodium carbonate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water; acetonitrile;

DOI:10.1021/jo0517388

Reference yield:

(5R)-3-benzyloxymethyl-5-[(4R)-2,2-dioxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline (877463-68-8) → (2R,3S)-1,3-O-benzylidene-1,3-dihydroxy-4-[(2R,4R,5R)-2-benzyloxymethyl-4,5-dihydroxypiperidinium-1-yl]butane-2-sulfate (877463-77-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 34 percent / sodium carbonate; hydrogen / Pd/C / methanol / 5 h / 20 °C

2: 86 percent / H₂SO₄ / dioxane; H₂O / 36 h / 50 °C

3: 74 percent / anhydrous sodium carbonate / tetrahydrofuran / 24 h / Heating

With sulfuric acid; hydrogen; sodium carbonate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water;

DOI:10.1021/jo0517388

upstream raw materials:

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

2,4-O-benzylidene-D-erythritol-1,3-cyclic-sulfate

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

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