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 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 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 
• 76375-60-5 (3R,4R,5R,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate 
• 10294-12-9 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-D-galactopyranose 
• 299190-04-8 Acetic acid (2R,3R,4R,5R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester 
• 109581-83-1 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α,β-D-galactopyranosyl chloride 

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 
• 1240386-62-2 (E)-4-(4-dimethoxymethylphenoxy)but-2-enyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 1202384-93-7 allyl 2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 1372788-84-5 (2R)-2,3-dihydroxypropyl 2-acetamido-3-O-acetyl-4,6-O-(R)-benzylidene-2-deoxy-β-D-glucopyranoside 
• 1372788-83-4 (2R)-2,3-dihydroxypropyl 2-acetamido-3-O-benzyl-4,6-O-(R)-benzylidene-2-deoxy-β-D-glucopyranoside 
• 1372788-70-9 (2R)-2,3-dihydroxypropyl 2-acetamido-4,6-O-(R)-benzylidene-2-deoxy-β-D-glucopyranoside 
• 1372788-97-0 allyl 2-acetamido-4,6-O-(R)-benzylidene-3-O-capryloyl-2-deoxy-β-D-glucopyranoside 
• 65372-01-2 2-methyl-(4-O-acetyl-3,6-di-O-benzyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline 
• 115491-86-6 Sodium; 2-{[(2S,4S)-4-((2R,3R,4R,5S,6R)-3-acetylamino-4-benzyloxy-6-benzyloxymethyl-5-sulfooxy-tetrahydro-pyran-2-yloxy)-1-benzyloxycarbonyl-pyrrolidine-2-carbonyl]-amino}-ethanesulfonate 
• 115516-58-0 (2S,4S)-4-((2R,3R,4R,5S,6R)-3-Acetylamino-4-benzyloxy-6-benzyloxymethyl-5-sulfooxy-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-(2,5-dioxo-pyrrolidin-1-yl) ester; compound with triethyl-amine 

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.

Glycosyl Aldehydes: New Scaffolds for the Synthesis of Neoglycoconjugates via Bioorthogonal Oxime Bond Formation

The straightforward preparation of glycosyl neoconjugates by oxime (or hydrazone) bond formation represents a key bioorthogonal tool in chemical biology. However, when this strategy is employed by reacting the reducing end of the glycan moiety, the configuration and the stereochemical information is lost due to partial (or complete) opening of the glycan cyclic hemiacetal and the formation of the corresponding opened tautomers. We have completed the synthesis of a library of glycosyl aldehydes to be used as scaffold for the synthesis of neoglycoconjugates via oxime bond formation. These glycosyl aldehydes constitute a simple and accessible alternative to avoid loss of chiral information when conjugating, by oxime (or hydrazone) bonds, the aldehyde functionality present at the reducing end of natural carbohydrates.

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