Benzyl N-Acetyl-4,6-O-benzylidene-α-D-muramic Acid, Methyl Ester

Base Information

• Chemical Name: Benzyl N-Acetyl-4,6-O-benzylidene-α-D-muramic Acid, Methyl Ester
• CAS No.: 104371-51-9
• Molecular Formula: C26H31NO8
• Molecular Weight: 485.5262
• Mol file: 104371-51-9.mol

Synonyms:Benzyl N-Acetyl-4,6-O-benzylidene-α-D-muramic Acid, Methyl Ester;[3(R)]-PhenylMethyl 2-(AcetylaMino)-2-deoxy-3-O-(2-Methoxy-1-Methyl-2-oxoethyl)-4,6-O-(phenylMethylene)-α-D-glucopyranoside;N-Acetyl-1-O-(phenylMethyl)-4,6-O-(phenylMethylene)-α-MuraMic Acid Methyl Ester

Chemical Property of Benzyl N-Acetyl-4,6-O-benzylidene-α-D-muramic Acid, Methyl Ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 205-206°C
• Refractive Index: 1.575
• Boiling Point: 675.963°C at 760 mmHg
• PKA: 13.96±0.70(Predicted)
• Flash Point: 362.609°C
• PSA: 101.55000
• Density: 1.27g/cm³
• LogP: 2.88460
• Storage Temp.: Refrigerator
• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

98%min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 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 Benzyl N-Acetyl-4,6-O-benzylidene-α-D-muramic Acid, Methyl Ester

There total 10 articles about Benzyl N-Acetyl-4,6-O-benzylidene-α-D-muramic Acid, Methyl Ester 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: 82.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-carboxyethyl>-α-D-glucopyranoside (2862-03-5) → Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-α-D-glucopyranoside (104371-51-9)

Guidance literature:

In methanol; diethyl ether; at 0 ℃; for 0.25h;

DOI:10.1016/0008-6215(94)90009-4

Reference yield:

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) → Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-α-D-glucopyranoside (104371-51-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 53 percent / acetyl chloride / 4 h / 75 °C

2.1: 58 percent / 10 percent H₂SO₄ / methanol / 0.05 h / 100 °C

3.1: Na / dioxane / 1 h / 90 - 95 °C

3.2: dioxane / 3 h / 60 - 65 °C

4.1: ethanol; diethyl ether

With sulfuric acid; sodium; acetyl chloride; In 1,4-dioxane; methanol; diethyl ether; ethanol; 1.1: Substitution / 2.1: benzylidenation / 3.1: deprotonation / 3.2: Alkylation / 4.1: Esterification;

Reference yield:

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-(methoxycarbonyl)ethyl>-α-D-glucopyranoside (104371-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Na / dioxane / 1 h / 90 - 95 °C

1.2: dioxane / 3 h / 60 - 65 °C

2.1: ethanol; diethyl ether

With sodium; In 1,4-dioxane; diethyl ether; ethanol; 1.1: deprotonation / 1.2: Alkylation / 2.1: Esterification;

upstream raw materials:

diazomethane

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

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

(R,S)-2-chloropropionic acid

Downstream raw materials:

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(S)-1-carboxyethyl>-α-D-glucopyranoside, Na salt

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

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

N-{2-O-[butyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-β-D-glucopyranosid-3-yl]-D-lactoyl}-L-alanyl-D-isoglutamine benzyl ester

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