N-<2-(Triphenylphosphonio)ethoxycarbonyl>phenylalanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester-chlorid

Base Information

• Chemical Name: N-<2-(Triphenylphosphonio)ethoxycarbonyl>phenylalanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester-chlorid
• CAS No.: 86040-98-4
• Molecular Formula: C₄₈H₅₅N₃O₁₄P*Cl
• Molecular Weight: 964.403
• Mol file: 86040-98-4.mol

Synonyms:N-<2-(Triphenylphosphonio)ethoxycarbonyl>phenylalanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester-chlorid

Chemical Property of N-<2-(Triphenylphosphonio)ethoxycarbonyl>phenylalanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester-chlorid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-<2-(Triphenylphosphonio)ethoxycarbonyl>phenylalanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester-chlorid

There total 3 articles about N-<2-(Triphenylphosphonio)ethoxycarbonyl>phenylalanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester-chlorid 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: 81.0%

Peoc-Phe-OH (63578-03-0) + O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester (66357-61-7) → N-<2-(Triphenylphosphonio)ethoxycarbonyl>phenylalanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester-chlorid (86040-98-4)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In chloroform; 1) 1 h, -15 deg C, 2) room temperature, 15 h;

DOI:10.1002/jlac.198319830303

Reference yield:

O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N-(benzyloxycarbonyl)serin-methylester (25644-83-1) → N-<2-(Triphenylphosphonio)ethoxycarbonyl>phenylalanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester-chlorid (86040-98-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / H₂ / 10percent Pd/C / methanol / 3 h / Ambient temperature

2: 81 percent / (ethyl)-2-ethoxy-1,2-dihydro-1-quinolinecarboxylate / CHCl₃ / 1) 1 h, -15 deg C, 2) room temperature, 15 h

With hydrogen; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; palladium on activated charcoal; In methanol; chloroform;

DOI:10.1002/jlac.198319830303

Reference yield:

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → N-<2-(Triphenylphosphonio)ethoxycarbonyl>phenylalanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester-chlorid (86040-98-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 30 percent / Hg(CN)2 / benzene

2: 94 percent / H₂ / 10percent Pd/C / methanol / 3 h / Ambient temperature

3: 81 percent / (ethyl)-2-ethoxy-1,2-dihydro-1-quinolinecarboxylate / CHCl₃ / 1) 1 h, -15 deg C, 2) room temperature, 15 h

With hydrogen; mercury(II) cyanide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; palladium on activated charcoal; In methanol; chloroform; benzene;

DOI:10.1002/jlac.198319830303

upstream raw materials:

Peoc-Phe-OH

O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester

O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N-(benzyloxycarbonyl)serin-methylester

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

Downstream raw materials:

Phenylalanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester

N-<2-(Triphenylphosphonio)ethoxycarbonyl>isoleucyl-phenylalanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester-chlorid