54400-75-8

Basic information

• Product Name: ALLYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE
• Synonyms: ALLYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE;Allyl2-acetamido-2-deoxy-a-D-glucopyranoside;2-AMINO-2-DEOXY-1,3,4,6-TETRA-O-ACETYL-A-D-GLUCOPYRANOSE HCL, 99% MIN., TLC;2-Propenyl-2-(acetylamino)-2-deoxy-alpha-D-glucopyranoside;2-Propen-1-yl 2-(acetylamino)-2-deoxy-α-D-glucopyranoside
• CAS NO: 54400-75-8
• Molecular Formula: C₁₁H₁₉NO₆
• Molecular Weight: 261.27
• Mol File: 54400-75-8.mol
• Article Data: 46

Chemical Properties

• Melting Point: 167-177°C
• Boiling Point: 541.7 °C at 760 mmHg
• Flash Point: 281.4 °C
• Appearance: /
• Density: 1.3 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: ALLYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ALLYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE(54400-75-8)
• EPA Substance Registry System: ALLYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE(54400-75-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 54400-75-8(Hazardous Substances Data)

Usage

General Description

ALLYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE is a chemical compound that is a derivative of glucopyranoside, a type of sugar. It is composed of an acetylated amino sugar, allyl group, and a glucopyranoside ring. ALLYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE has potential applications in the field of medicinal chemistry, particularly in the development of glycoconjugates for various biological studies. It may also have potential as a building block for the synthesis of more complex carbohydrate derivatives. Due to its structure and properties, ALLYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE may have potential biological activities and therapeutic uses, although further research is needed to fully understand its potential in these areas.

Upstream product

• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 107-18-6 allyl alcohol 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 1040191-33-0 N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 106-95-6 allyl bromide 
• 20907-32-8 sodium allyloxide 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 63064-48-2 allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 10378-06-0 acetic acid (3aR,5R,6R,7R,7aR)-6-acetoxy-5-acetoxymethyl-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-7-yl ester 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-galactopyranose 
• 14257-79-5 β-D-galactosamine hydrochloride 
• 4163-60-4 β-D-galactose peracetate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 

Downstream Products

• 74984-84-2 prop-2-en-1-yl 2-(acetylamino)-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 63064-49-3 allyl 2-acetamido-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 613672-67-6 allyl 2-acetamido-4,6-O-(4-fluorobenzylidene)-2-deoxy-α-D-glucopyranoside 
• 70832-36-9 propyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 224964-33-4 allyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 251324-19-3 allyl 2-acetamido-3-O-acetyl-4-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 251324-21-7 allyl 2-acetamido-3-O-acetyl-6-azido-4-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 251324-20-6 allyl 2-acetamido-3-O-acetyl-4-O-benzyl-2-deoxy-6-O-tosyl-α-D-glucopyranoside 
• 246513-17-7 allyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-β-D-glucopyranoside 
• 92949-55-8 allyl 6-O-<3,4,6-tri-O-acetyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranoside 
• 92949-51-4 allyl 2-acetamido-3,6-di-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 92949-54-7 Benzoic acid (2R,3R,4R,5S,6R)-2-allyloxy-3-amino-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-amino-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester 
• 114360-80-4 allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside 
• 92949-56-9 allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside 

Relevant articles and documents

2-Acetamido-2-deoxy-l-iminosugar C-Alkyl and C-Aryl Glycosides: Synthesis and Glycosidase Inhibition

The synthesis of a series of six-membered 2-acetamido l-iminosugar C-alkyl and C-aryl glycosides is reported. A diastereoselective sugar-ring enlargement/C-alkylation (or arylation) /ring-contraction sequence applied to d-gluco- and d-manno-configured 2-acetamido azidolactols provides new l-iminosugar C-glycosides. The 1,2-trans stereocontrolled introduction of the pseudoanomeric substituent in these heterocycles strongly suggests a NHAc neighbouring-group participation. In their deprotected form, the nine iminosugars exhibit moderate hexosaminidases and β-glucuronidase inhibition.

Synthesis and biological evaluation of novel mono- and bivalent ASGP-R-targeted drug-conjugates

Asialoglycoprotein receptor (ASGP-R) is a promising biological target for drug delivery into hepatoma cells. Nevertheless, there are only few examples of small-molecule conjugates of ASGP-R selective ligand equipped by a therapeutic agent for the treatment of hepatocellular carcinoma (HCC). In the present work, we describe a convenient and versatile synthetic approach to novel mono- and multivalent drug-conjugates containing N-acetyl-2-deoxy-2-aminogalactopyranose and anticancer drug – paclitaxel (PTX). Several molecules have demonstrated high affinity towards ASGP-R and good stability under physiological conditions, significant in vitro anticancer activity comparable to PTX, as well as good internalization via ASGP-R-mediated endocytosis. Therefore, the conjugates with the highest potency can be regarded as a promising therapeutic option against HCC.

Exploring the Structural Space of the Galectin-1–Ligand Interaction

Galectin-1 is a tumor-associated protein recognizing the Galβ1-4GlcNAc motif of cell-surface glycoconjugates. Herein, we report the stepwise expansion of a multifunctional natural scaffold based on N-acetyllactosamine (LacNAc). We obtained a LacNAc mimeti