N-ACETYL-1-CHLORO-3,4,6-TRI-O-ACETYL-GLUCOSAMINIDE

Base Information

• Chemical Name: N-ACETYL-1-CHLORO-3,4,6-TRI-O-ACETYL-GLUCOSAMINIDE
• CAS No.: 51236-40-9
• Molecular Formula: C₁₄H₂₀ClNO₈
• Molecular Weight: 365.768
• Mol file: 51236-40-9.mol

Synonyms:N-ACETYL-1-CHLORO-3,4,6-TRI-O-ACETYL-GLUCOSAMINIDE

Chemical Property of N-ACETYL-1-CHLORO-3,4,6-TRI-O-ACETYL-GLUCOSAMINIDE

Chemical Property:

• PSA: 120.72000
• LogP: 0.72160

Purity/Quality:

98% ^*data from raw suppliers

2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosyl chloride - Stabilised with 2% CaCO3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-ACETYL-1-CHLORO-3,4,6-TRI-O-ACETYL-GLUCOSAMINIDE

There total 8 articles about N-ACETYL-1-CHLORO-3,4,6-TRI-O-ACETYL-GLUCOSAMINIDE 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-glucosamine

acetyl chloride

1,1-dichloroethane

D-glucosamine hydrochloride

Downstream raw materials:

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose

2-(4-benzyloxyphenyl)ethyl 2-acetamido-2-deoxy-β-D-glucopyranoside

2-(4-hydroxyphenyl)ethyl 2-acetamido-2-deoxy-β-D-glucopyranoside

C₂₉H₃₅NO₁₀