28738-44-5

Basic information

• Product Name: Allyl 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy--D-glucopyranoside
• Synonyms: 2-Propenyl 2-(Acetylamino)-2-deoxy--D-glucopyranoside 3,4,6-Triacetate;Allyl 2-Acetamido-2-deoxy--D-glucopyranoside 3,4,6-Triacetate;Allyl 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy--D-glucopyranoside;Allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside;Allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside;[(3S,4R,5S,6R)-5-acetamido-3,4-diacetoxy-6-allyloxy-tetrahydropyran-2-yl]methyl acetate
• CAS NO: 28738-44-5
• Molecular Formula: C₁₇H₂₅NO₉
• Molecular Weight: 387.38
• EINECS: 1533716-785-6
• Product Categories: Carbohydrates & Derivatives
• Mol File: 28738-44-5.mol
• Article Data: 26

Chemical Properties

• Melting Point: 151-157°C (dec.)
• Boiling Point: 531.336 °C at 760 mmHg
• Flash Point: 275.142 °C
• Appearance: /
• Density: 1.233 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.492
• Storage Temp.: Refrigerator
• Solubility: MethanolMethanol
• PKA: 13.67±0.70(Predicted)
• CAS DataBase Reference: Allyl 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy--D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Allyl 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy--D-glucopyranoside(28738-44-5)
• EPA Substance Registry System: Allyl 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy--D-glucopyranoside(28738-44-5)

Safety Data

• Hazardous Substances Data: 28738-44-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1/C17H25NO9/c1-6-7-23-17-14(18-9(2)19)16(26-12(5)22)15(25-11(4)21)13(27-17)8-24-10(3)20/h6,13-17H,1,7-8H2,2-5H3,(H,18,19)/t13?,14-,15+,16+,17+/m0/s1

Upstream product

• 108-24-7 acetic anhydride 
• 126777-92-2 3,4,6-tetra-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranosyl azide 
• 107-18-6 allyl alcohol 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 134160-64-8 4',5'-epoxypentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 10294-12-9 2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 
• 106-95-6 allyl bromide 
• 3006-60-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester 
• 297132-68-4 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl diphenylphosphinate 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 54400-75-8 allyl 2-acetamido-2-deoxy-β-D-glucopyranoside 

Downstream Products

• 54400-75-8 allyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 10294-12-9 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranose 
• 54400-75-8 allyl-2-acetamido-2-deoxy-β-D-galactopyranoside 
• 325962-11-6 3-benzylthiopropyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 508194-14-7 allyl 2-acetamido-3-O-acetyl-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 63064-49-3 allyl 2-acetamido-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 508194-16-9 allyl 2-acetamido-3-O-benzyl-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 321679-22-5 (R)-2,3-epoxypropyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 321679-30-5 (R)-3-azido-2-hydroxypropyl 2-acetamido-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 508194-19-2 allyl 2-acetamido-(R)-4,6-O-benzylidene-2-deoxy-2-N-3-O-methylidene-β-D-glucopyranoside 
• 508194-15-8 allyl 2-acetamido-(R)-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-glucopyranoside 
• 508194-17-0 allyl 2-acetamido-(R)-4,6-O-benzylidene-2-deoxy-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside 

Relevant articles and documents

OLIGONUCLEOTIDE CONJUGATE COMPOSITIONS AND METHODS OF USE

The disclosure relates to GalNAc moieties comprising at least one GalNAc monomer. The disclosure also relates to GalNAc-oligonucleotide conjugates comprising GalNAc moieties and oligonucleotides, e.g., saRNAs or siRNAs useful in regulating the expression of a target gene. Methods of using the GalNAc- oligonucleotide conjugates are also provided.

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