benzyl N-(benzyloxycarbonyl)-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-L-serinate

Base Information

• Chemical Name: benzyl N-(benzyloxycarbonyl)-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-L-serinate
• CAS No.: 1431370-40-9
• Molecular Formula: C₄₄H₃₉NO₁₂
• Molecular Weight: 773.793
• Mol file: 1431370-40-9.mol

Synonyms:benzyl N-(benzyloxycarbonyl)-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-L-serinate

Chemical Property of benzyl N-(benzyloxycarbonyl)-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-L-serinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl N-(benzyloxycarbonyl)-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-L-serinate

There total 8 articles about benzyl N-(benzyloxycarbonyl)-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-L-serinate 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%

N-benzyloxycarbonyl-L-serine benzyl ester (21209-51-8) + 3,5-di-O-benzoyl-β-D-arabinofuranoside-prop-2-ynyl-1,2-orthobenzoate (1431370-34-1) → benzyl N-(benzyloxycarbonyl)-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-L-serinate (1431370-40-9)

Guidance literature:

With gold(III) chloride; In dichloromethane; at 25 ℃; for 2h; Molecular sieve; Inert atmosphere;

DOI:10.1021/ol400931p

Reference yield:

methyl D-arabinofuranoside (79083-42-4) → benzyl N-(benzyloxycarbonyl)-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-L-serinate (1431370-40-9)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 0 - 20 °C / Inert atmosphere

2: Acetyl bromide; methanol / dichloromethane / 2 h / 0 °C / Inert atmosphere

3: 2,6-dimethylpyridine; tetra-(n-butyl)ammonium iodide / dichloromethane / 4 h / 20 °C / Inert atmosphere

4: gold(III) chloride / dichloromethane / 2 h / 25 °C / Molecular sieve; Inert atmosphere

With pyridine; 2,6-dimethylpyridine; methanol; gold(III) chloride; Acetyl bromide; tetra-(n-butyl)ammonium iodide; In dichloromethane;

DOI:10.1021/ol400931p

Reference yield:

2,3,5-tri-O-benzoyl-α,β-D-arabinofuranosyl bromide (56271-35-3) → benzyl N-(benzyloxycarbonyl)-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-L-serinate (1431370-40-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-dimethylpyridine; tetra-(n-butyl)ammonium iodide / dichloromethane / 4 h / 20 °C / Inert atmosphere

2: gold(III) chloride / dichloromethane / 2 h / 25 °C / Molecular sieve; Inert atmosphere

With 2,6-dimethylpyridine; gold(III) chloride; tetra-(n-butyl)ammonium iodide; In dichloromethane;

DOI:10.1021/ol400931p

upstream raw materials:

N-benzyloxycarbonyl-L-serine benzyl ester

3,5-di-O-benzoyl-β-D-arabinofuranoside-prop-2-ynyl-1,2-orthobenzoate

D-arabinofuranose

methyl D-arabinofuranoside