2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE

Base Information

• Chemical Name: 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE
• CAS No.: 41355-44-6
• Molecular Formula: C14H20 Cl N O8
• Molecular Weight: 365.768
• Mol file: 41355-44-6.mol

Synonyms:Galactosylchloride, 2-acetamido-2-deoxy-, 3,4,6-triacetate (6CI); 2-Acetamido-2-deoxy-a-D-galactosylchloride 3,4,6-triacetate; N,3,4,6-O-Tetraacetyl-a-D-galactosaminylchloride

Chemical Property of 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE

Chemical Property:

• Melting Point: 131-136 °C (decomp)
• Boiling Point: 516.4±50.0 °C(Predicted)
• PKA: 13.22±0.70(Predicted)
• PSA: 117.23000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 0.27220

Purity/Quality:

98.0%min ^*data from raw suppliers

2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-a-D-galactopyranosyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N,3,4,6-O-Tetraacetyl-α-D-galactosaminyl chloride is used in the preparation of selenenylsulfide-linked glycopeptides and glycoproteins.

Technology Process of 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE

There total 9 articles about 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE 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: 68.0%

N-acetyl-D-glucosamine (14131-68-1) + acetyl chloride (75-36-5) → 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl chloride (3068-34-6,41355-44-6,51236-40-9,74081-14-4,79897-03-3,100759-09-9,109581-83-1,38874-23-6)

Guidance literature:

at 20 ℃;

Reference yield: 60.0%

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) + acetyl chloride (75-36-5) → 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride (3068-34-6,38874-23-6,41355-44-6,51236-40-9,74081-14-4,79897-03-3,100759-09-9,109581-83-1)

Guidance literature:

at 20 ℃; for 48h;

DOI:10.1002/cplu.201200014

Reference yield:

acetic anhydride (108-24-7) + D-(+)-glucosamine hydrochloride (66-84-2) → 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl chloride (3068-34-6,41355-44-6,51236-40-9,74081-14-4,79897-03-3,100759-09-9,109581-83-1,38874-23-6) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6)

Guidance literature:

D-(+)-glucosamine hydrochloride; With sodium methylate; In methanol; at 20 ℃; for 1h;

acetic anhydride; In methanol; at 0 - 20 ℃;

With acetyl chloride; at 0 ℃; optical yield given as %de; Inert atmosphere; Reflux;

DOI:10.1021/ja104994d

upstream raw materials:

N-acetyl-D-galactosamine

acetyl chloride

N-Acetyl-D-glucosamine

1,1-dichloroethane

Downstream raw materials:

phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside

4-methylumbelliferyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside

2-[2-(2-Azidoethoxy)ethoxy]ethyl 3,4,6-tri-O-acetyl-2-N-acetamido-2-deoxy-β-D-glucopyranoside

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide