2-(3-ACETAMIDO-2-BENZYL-4,6,OBENZYLIDENE-ALPHA-D-GLUCOPYRNOSID-4-YLOXY)PROPIONIC ACID

Base Information

• Chemical Name: 2-(3-ACETAMIDO-2-BENZYL-4,6,OBENZYLIDENE-ALPHA-D-GLUCOPYRNOSID-4-YLOXY)PROPIONIC ACID
• CAS No.: 2862-03-5
• Molecular Formula: C25H29NO8
• Molecular Weight: 471.507
• Mol file: 2862-03-5.mol

Synonyms:AC-A-BENZYL-4,6-O-BENZYLIDENE-MURAMIC ACID;Benzyl N-Acetyl-4,6-O-benzylidene-Alpha-D-muramic Acid;Benzyl N-Acetyl-4,6-O-benzylidene-α-D-muramic Acid;Benzyl N-Acetyl-4,6-O-benzylidene-a-D-muramic Acid;2-(3-ACETAMIDO-2-BENZYL-4,6,O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSID-4-YLOXY)PROPANOIC ACID;ALPHA-BENZYL-4,6-O-BENZYLIDENE-MURAMIC ACID;BENZYL 2-ACETAMIDO-4,6-O-BENZYLIDENE-2-DEOXY-A-D-MURAMIC ACID;

Chemical Property of 2-(3-ACETAMIDO-2-BENZYL-4,6,OBENZYLIDENE-ALPHA-D-GLUCOPYRNOSID-4-YLOXY)PROPIONIC ACID

Chemical Property:

• Melting Point: 237-239° C
• PSA: 112.55000
• LogP: 2.79620
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO, Methanol

Purity/Quality:

99.3% ^*data from raw suppliers

BenzylN-Acetyl-4,6-O-benzylidene-α-D-muramicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Benzyl derivative of muramic acid. The N-acetyl derivative of muramic acid is an amino sugar found in peptidoglycan, the main skeletal component of both Gram positive and Gram negative bacterial cell wall.

Technology Process of 2-(3-ACETAMIDO-2-BENZYL-4,6,OBENZYLIDENE-ALPHA-D-GLUCOPYRNOSID-4-YLOXY)PROPIONIC ACID

There total 7 articles about 2-(3-ACETAMIDO-2-BENZYL-4,6,OBENZYLIDENE-ALPHA-D-GLUCOPYRNOSID-4-YLOXY)PROPIONIC ACID 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: 98.0%

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-α-D-glucopyranoside (104371-51-9) → Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-carboxyethyl>-α-D-glucopyranoside (2862-03-5)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 40 ℃; for 1h;

DOI:10.1002/jlac.198619860104

Reference yield: 84.0%

(S)-2-chloropropanoic acid (29617-66-1) + benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside (13343-63-0) → Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-carboxyethyl>-α-D-glucopyranoside (2862-03-5)

Guidance literature:

With sodium hydride; In 1,4-dioxane; at 60 ℃; for 0.833333h;

DOI:10.1246/bcsj.59.3207

Reference yield:

L-2-chloropropionic acid sodium salt (74533-11-2) + benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside (13343-63-0) → Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-carboxyethyl>-α-D-glucopyranoside (2862-03-5)

Guidance literature:

benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside; With sodium; In 1,4-dioxane; at 90 - 95 ℃; for 1h;

L-2-chloropropionic acid sodium salt; In 1,4-dioxane; at 60 - 65 ℃; for 3h;

upstream raw materials:

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-α-D-glucopyranoside

(S)-2-chloropropanoic acid

benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside

Ethyl 2-bromopropionate

Downstream raw materials:

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-α-D-glucopyranoside

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-carboxyethyl>-α-D-glucopyranoside, HONB ester

(R)-2-{(S)-2-[(R)-2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionylamino]-propionylamino}-pentanedioic acid 1-amide 5-octylamide

benzyl 2-acetamido-2-deoxy-3-O--β-D-glucopyranoside