3946-01-8

Basic information

• Product Name: METHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE
• Synonyms: METHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE;GLCNAC1-BETA-OME;METHYL 2-ACETAMIDO-2-DEOXY-B-D- &;GlcNAc1-OMe;Methyl2-acetamido-2-deoxy-b-D-glucopyranoside;Methyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside;b-D-Glucopyranoside, Methyl 2-(acetylaMino)-2-deoxy-;beta-Methyl N-acetyl-D-glucosamine
• CAS NO: 3946-01-8
• Molecular Formula: C₉H₁₇NO₆
• Molecular Weight: 235.23
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 3946-01-8.mol
• Article Data: 66

Chemical Properties

• Melting Point: 204-206°C
• Appearance: /
• Density: 1.36
• Storage Temp.: 2-8°C
• Solubility: Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: METHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(3946-01-8)
• EPA Substance Registry System: METHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(3946-01-8)

Safety Data

• Hazardous Substances Data: 3946-01-8(Hazardous Substances Data)

Usage

Description

METHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE, with the CAS number 3946-01-8, is a white crystalline solid that serves as a valuable compound in the realm of organic synthesis. Its unique chemical structure allows it to be a versatile building block for the creation of various complex organic molecules.

Uses

Used in Organic Synthesis:
METHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is used as a synthetic building block for the development of complex organic molecules. Its chemical properties make it a suitable candidate for use in the synthesis of a wide range of compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, METHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is used as a key intermediate in the synthesis of various drugs. Its unique structure allows for the creation of novel drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
METHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is also utilized in the agrochemical industry for the synthesis of new compounds with potential applications in crop protection and pest control.
Used in Research and Development:
In the field of research and development, METHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE serves as an important compound for studying the properties and reactivity of similar molecules. This knowledge can be applied to the design and development of new materials and products across various industries.

Upstream product

• 186581-53-3 diazomethane 
• 67-56-1 methanol 
• 60-29-7 diethyl ether 
• 7512-17-6 2-acetamido-2-deoxy-D-glucose 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 120489-51-2 methyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-β-D-glucopyranoside 
• 2771-48-4 methyl 2-acetamido-3,4,6-O-triacetyl-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 
• 463-51-4 Ketene 
• 60667-89-2 N-((2S,3R,4R,5S,6R)-2-Bromo-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide 
• 108-24-7 acetic anhydride 
• 384346-98-9 methyl 3-O-tert-butyldimethylsilyl-4,6-O-p-methoxybenzylidene-2-deoxy-2-trifluoroacetamido-β-D-glucopyranoside 
• 117177-19-2 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline 

Downstream Products

• 6619-04-1 N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide 
• 885458-78-6 methyl-[2-(2,4-dinitro-anilino)-2-deoxy-β-D-glucopyranoside] 
• 88295-36-7 1-O-Methyl-2-N-acetylamino-2-deoxy-4,6-O-benzyliden-α,β-D-glucopyranosid 
• 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 
• 42756-57-0 methyl 2-acetamido-2-deoxy-6-O-trityl-D-glucopyranoside 
• 10300-76-2 methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 132488-48-3 methyl 2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside 
• 10583-67-2 methyl 2-(N-acetylamino)-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 87171-52-6 methyl 2-acetamido-3,4,6-tri-O-(p-bromobenzoyl)-2-deoxy-β-D-glucopyranoside 
• 100836-88-2 Galβ(1-3)GlcNAcβ(1-)OCH3 
• 68774-40-3 N-acetyllactosamine methyl glycoside 
• 136198-40-8 methyl-N,N'-diacetyl-β-chitobioside 

Relevant articles and documents

Amide Cis-trans isomerization in aqueous solutions of methyl N -Formyl- d -glucosaminides and Methyl N -Acetyl- d -glucosaminides: Chemical equilibria and exchange kinetics

Amide cis-trans isomerization (CTI) in methyl 2-deoxy-2-acylamido-d- glucopyranosides was investigated by 1H and 13C NMR spectroscopy. Singly 13C-labeled methyl 2-deoxy-2-formamido-d- glucopyranoside (MeGlcNFm) anomers provided standard 1H and 13C chemical shifts and 1H-1H and 13C-13C spin-coupling constants for cis and trans amides that are detected readily in aqueous solution. Equipped with this information, doubly 13C-labeled methyl 2-deoxy-2-acetamido-d-glucopyranoside (MeGlcNAc) anomers were investigated, leading to the detection and quantification of cis and trans amides in this biologically important aminosugar. In comparison to MeGlcNFm anomers, the percentage of cis amide in aqueous solutions of MeGlcNAc anomers is small (～23% for MeGlcNFm versus ～1.8% for MeGlcNAc at 42 °C) but nevertheless observable with assistance from 13C-labeling. Temperature studies gave thermodynamic parameters δG°, δH°, and δS° for cis-trans interconversion in MeGlcNFm and MeGlcNAc anomers. Cis/trans equilibria depended on anomeric configuration, with solutions of α-anomers containing less cis amide than those of β-anomers. Confirmation of the presence of cis amide in MeGlcNAc solutions derived from quantitative 13C saturation transfer measurements of CTI rate constants as a function of solution temperature, yielding activation parameters Eact, δG° ?, δH°-, and δS° ? for saccharide CTI. Rate constants for the conversion of trans to cis amide in MeGlcNFm and MeGlcNAc anomers ranged from 0.02 to 3.59 s-1 over 31-85 °C, compared to 0.24-80 s-1 for the conversion of cis to trans amide over the same temperature range. Energies of activation ranged from 16-19 and 19-20 kcal/mol for the cis → trans and trans → cis processes, respectively. Complementary DFT calculations on MeGlcNFm and MeGlcNAc model structures were conducted to evaluate the effects of an acyl side chain and anomeric structure, as well as C2-N2 bond rotation, on CTI energetics. These studies show that aqueous solutions of GlcNAc-containing structures contain measurable amounts of both cis and trans amides, which may influence their biological properties.

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Stoichiometric C6-oxidation of hyaluronic acid by oxoammonium salt TEMPO+Cl- in an aqueous alkaline medium

This paper reports the selective oxidation of hyaluronic acid (HA) by stoichiometric quantity of 2,2,6,6-tetramethylpiperidine-1-oxoammonium chloride (TEMPO+) in aqueous alkaline medium. High efficiency of the HA oxidation and quantitative yield of carboxy-HA per starting TEMPO+, as well as unusual behavior of the oxidation system generating an oxygen upon alkali-induced oxoammonium chloride decomposition are demonstrated. The scheme for HA oxidation involving both TEMPO+ and oxygen produced upon the TEMPO+Cl- decomposition and/or air oxygen is proposed. For comparison, the data on stoichiometric oxidation of such substrates as dermatan sulfate, water-soluble potato starch, methyl 2-acetamido-2-deoxy-β-d-glucopyranoside and ethanol are presented.

O-Acetylated sugars in the gas phase: stability, migration, positional isomers and conformation

O-Acetylations are functional modifications which can be found on different hydroxyl groups of glycans and which contribute to the fine tuning of their biological activity. Localizing the acetyl modifications is notoriously challenging in glycoanalysis, in particular because of their mobility: loss or migration of the acetyl group may occur through the analytical workflow. Whereas migration conditions in the condensed phase have been rationalized, little is known about the suitability of Mass Spectrometry to retain and resolve the structure of O-acetylated glycan isomers. Here we used the resolving power of infrared ion spectroscopy in combination with ab initio calculations to assess the structure of O-acetylated monosaccharide ions in the gaseous environment of a mass analyzer. N-Acetyl glucosamines were synthetized with an O-acetyl group in positions 3 or 6, respectively. The protonated ions produced by electrospray ionization were observed by mass spectrometry and their vibrational fingerprints were recorded in the 3 μm range by IRMPD spectroscopy (InfraRed Multiple Photon Dissociation). Experimentally, the isomers show distinctive IR fingerprints. Additionally, ab initio calculations confirm the position of the O-acetylation and resolve their gas phase conformation. These findings demonstrate that the position of O-acetyl groups is retained through the transfer from solution to the gas phase, and can be identified by IRMPD spectroscopy.

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

Synthesis of glucosamine vinyl ether derivative and its deuterated analog

The use of calcium carbide (in the presence of H2O) as a source of acetylene in the reaction with methyl 2-amino-4,6-O-benzylidene-2-deoxy-β-d-glucopyranoside under superbasic conditions (KF, KOH, DMSO, 130 °C, 3 h) led to the corresponding vin