22256-76-4

Basic information

• Product Name: Methyl N-Acetyl-β-D-glucosaMinide
• Synonyms: Methyl N-Acetyl-β-D-glucosaMinide;Methyl 2-Acetamido-2-deoxy-β-D-galactopyranoside;β-D-Galactopyranoside, methyl 2-(acetylamino)-2-deoxy-;N-((2R,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3-yl)acetamide
• CAS NO: 22256-76-4
• Molecular Formula: C₉H₁₇NO₆
• Molecular Weight: 235.23438
• Mol File: 22256-76-4.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: Methyl N-Acetyl-β-D-glucosaMinide(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl N-Acetyl-β-D-glucosaMinide(22256-76-4)
• EPA Substance Registry System: Methyl N-Acetyl-β-D-glucosaMinide(22256-76-4)

Safety Data

• Hazardous Substances Data: 22256-76-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Methyl N-Acetyl-β-D-glucosaMinide is used as a synthetic building block for the preparation of various complex carbohydrates, glycoconjugates, and bioactive molecules. Its ability to form stable glycosidic linkages with other monosaccharides and biomolecules makes it a valuable compound in the field of organic synthesis.
Used in Pharmaceutical Industry:
Methyl N-Acetyl-β-D-glucosaMinide is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly those targeting glycobiology-related diseases. Its role in the development of novel therapeutics for conditions such as cancer, inflammatory disorders, and infectious diseases is of significant interest to researchers and pharmaceutical companies.
Used in Research and Development:
In the field of research and development, Methyl N-Acetyl-β-D-glucosaMinide is employed as a valuable tool for studying the structure, function, and interactions of glycoproteins and other glycoconjugates. Its use in the design and synthesis of glycomimetic compounds and glycosylated drugs aids in understanding the role of carbohydrates in biological processes and the development of new therapeutic strategies.
Used in Diagnostics:
Methyl N-Acetyl-β-D-glucosaMinide is also utilized in the development of diagnostic tools and assays for the detection and analysis of glycoproteins and other carbohydrate-containing biomolecules. Its incorporation into diagnostic reagents and kits helps in the identification and quantification of specific glycoforms, which can be crucial for disease diagnosis and monitoring.

Upstream product

• 50605-02-2 methyl 2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-galactopyranoside 
• 67-56-1 methanol 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 10036-64-3 N-acetyl-D-glucosamine 
• 72-87-7 N-acetyl-D-glucosamine 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 75-36-5 acetyl chloride 
• 80040-79-5 3,4,6-tri-O-benzyl-D-galactal 
• 21193-75-9 D-galactal 
• 4098-06-0 triacetyl-D-galactal 
• 10583-67-2 Methyl-2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosid 
• 211621-55-5 3,4,6-tri-O-benzyl-2-nitro-D-galactal 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-galactopyranose 
• 41355-44-6 2-acetamido-2,4,6,-tri-O-acetyl-1-chloro-1,2-dideoxy-α-D-galactopyranose 

Downstream Products

• 129903-64-6 methyl 2-acetamido-3,4,6-tri-O-(p-bromobenzoyl)-2-deoxy-β-D-galactopyranoside 
• 2771-48-4 methyl 2-acetamido-3,4,6-O-triacetyl-2-deoxy-β-D-glucopyranoside 
• 2595-39-3 methyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside 
• 3006-60-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester 
• 1370587-63-5 methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-xylo-hexapyranoside-4-ulose 
• 1370586-83-6 methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-xylo-hexapyranosid-4-ulose 
• 1370586-92-7 methyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-glucopyranoside 
• 176690-90-7 methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside 
• 269065-36-3 methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside 
• 1281971-18-3 methyl 2-(N-acetylamino)-3,4,6-tri-O-(4-tert-butylbenzyl)-2-deoxy-α-D-glucopyranoside 
• 1423122-14-8 methyl 3,4,6-Tri-O-(4-tert-butylbenzyl)-2-deoxy-2-(L-prolylamino)-α-D-glucopyranoside 
• 1423122-13-7 C₃₈H₄₈N₂O₈ 
• 10583-67-2 methyl 2-(N-acetylamino)-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 154125-86-7 methyl 2-deoxy-3,4,6-tri-O-benzyl-2-(N-acetylamino)-α-D-glucopyranoside 

Relevant articles and documents

HYDROGEN FLUORIDE-CATALYZED FORMATION OF GLYCOSIDES. PREPARATION OF METHYL 2-ACETAMIDO-2-DEOXY-β-D-GLUCO- AND -β-D-GALACTO-PYRANOSIDES, AND OF β-(1->6)-LINKED 2-ACETAMIDO-2-DEOXY-D-GLUCO- AND -D-GALACTO-PYRANOSYL OLIGOSACCHARIDES

Dissolution of 2-acetamido-2-deoxy-D-glucose (1) or -D-galactose (2) in anhydrous hydrogen fluoride, followed by addition of methanol, gave stereospecifically the corresponding methyl β-D-glycopyranosides 7 and 8.When solutions of 1 or 2 in hydrogen fluoride were slowly evaporated, mixtures of exclusively β-D-(1->6)-linked di- to hexa-saccharides containing 2-acetamido-2-deoxy-glucosyl (9) and -galactosyl (10) residues were obtained; these were separated by gel permeation chromatography to give pure products.Compounds 7 and 9 were also obtained when solutions of chitin were treated under appropriate conditions.

IN VIVO ASSEMBLY OF ASGPR BINDING THERAPEUTICS

Compounds are provided that assemble together in vivo to form an ASGPR-binding compound that has an asialoglycoprotein receptor (ASGPR) binding ligand bound to an extracellular protein binding ligand for the selective degradation of the target extracellular protein in vivo to treat disorders mediated by the extracellular protein.

Design, physico-chemical characterization andin vitrobiological activity of organogold(iii) glycoconjugates

To develop new metal-based glycoconjugates as potential anticancer agents, four organometallic gold(iii)-dithiocarbamato glycoconjugates of the type [AuIII(2-Bnpy)(SSC-Inp-GlcN)](PF6) (2-Bnpy: 2-benzylpyridine; Inp: isonipecotic moie

Synthetic development of sugar amino acid oligomers towards novel podophyllotoxin analogues

In this work, we have developed an approach for the synthesis of sugar amino acid oligomers based on the glucosamine scaffold. We found that the solid-phase approach was unsuccessful for the preparation of sugar amino acid oligomers and the limitation of

ASGPR-BINDING COMPOUNDS FOR THE DEGRADATION OF EXTRACELLULAR PROTEINS

Compounds and compositions that have an asialoglycoprotein receptor (ASGPR) binding ligand bound to an extracellular protein binding ligand for the selective degradation of the target extracellular protein in vivo to treat disorders mediated by the extracellular protein are described.

Ultrasonication-Assisted Synthesis of a d-Glucosamine-Based β-CD Inclusion Complex and Its Application as an Aqueous Heterogeneous Organocatalytic System

For the first time, an inclusion complex has been crafted between a carbohydrate-based molecule and a β-cyclodextrin (CD) hydrophobic cavity for asymmetric catalytic applications. This novel d-glucosamine-based inclusion compound has been synthesized in h

Ring-Opening Reactions of the N-4-Nosyl Hough-Richardson Aziridine with Nitrogen Nucleophiles

Dinosylated α-d-glucopyranoside was directly transformed into α-d-altropyranosides via in situ formed N-4-nosyl Hough-Richardson aziridine with nitrogen nucleophiles under mild conditions in fair to excellent yields. The scope of the aziridine ring-opening reaction was substantially broadened contrary to the conventional methods introducing solely the azide anion at high temperatures. If necessary, the N-4-nosyl Hough-Richardson aziridine can be isolated by filtration in a very good yield and high purity.

Sugar derived alkamine catalytic imine reduction method

The invention discloses a method used for catalytic reduction of imine with saccharide-derivatized amino alcohol. According to the method, imine is taken as a substrate. The method comprises following steps: 1) imine and saccharide-derivatized amino alcohol are dissolved in an organic solvent I, wherein molar ratio of imine to saccharide-derivatized amino alcohol ranges from 100:1-20; 2) trichlorosilane with 1.5 to 5 times equivalent weights is added into a solution obtained via step 1) dropwise, an obtained mixture is stirred and reacted for 12 to 36h at a temperature of -20 to 40 DEG C, and a saturated sodium bicarbonate solution is used for quenching; 3) a material obtained via step 2) is extracted with an organic solvent II, and is subjected to column chromatography isolation so as to obtain amine compounds.

Synthetic heparin pentasaccharides

Preparation and use of synthetic monosaccharides, disaccharides, trisaccharides, tetrasaccharides and pentasaccharides useful for the preparation of synthetic heparinoids.

N-acetylgalactosamine green synthetic method

The present invention discloses a N-acetylgalactosamine green synthetic method. According to the method, N-acetylglucosamine as a raw material is successively condensed with an alcohol and pivaloyl chloride, and then N-acetylgalactosamine can be obtained