6983-36-4

Basic information

• Product Name: N-acetylglucopyranosylamine
• Synonyms: N-acetylglucopyranosylamine
• CAS NO: 6983-36-4
• Molecular Formula: C₈H₁₅NO₆
• Molecular Weight: 221.21
• Mol File: 6983-36-4.mol

Chemical Properties

• Boiling Point: 562.1°C at 760 mmHg
• Flash Point: 293.8°C
• Appearance: /
• Density: 1.5g/cm³
• Vapor Pressure: 5.62E-15mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: N-acetylglucopyranosylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-acetylglucopyranosylamine(6983-36-4)
• EPA Substance Registry System: N-acetylglucopyranosylamine(6983-36-4)

Safety Data

• Hazardous Substances Data: 6983-36-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H15NO6/c1-3(11)9-8-7(14)6(13)5(12)4(2-10)15-8/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8?/m1/s1

Upstream product

• 7284-37-9 D-glucopyranosyl amine 
• 108-24-7 acetic anhydride 
• 57820-45-8 1-Desoxy-N-hydroxy-β-D-glucopyranosylamin 
• 127-17-3 2-oxo-propionic acid 
• 2280-44-6 D-Glucose 
• 75-05-8 acetonitrile 
• 20379-59-3 D-glucopyranosyl azide 
• 507-09-5 tiolacetic acid 
• 6983-35-3 1-acetamido-2,3,4,6-tetraacetyl-1-deoxy-β-D-glucopyranose 
• 463-51-4 Ketene 

Downstream Products

• 6983-35-3 1-acetamido-2,3,4,6-tetraacetyl-1-deoxy-β-D-glucopyranose 
• 88-75-5 2-hydroxynitrobenzene 

Relevant articles and documents

β-1-N-acetamido-D-glucopyranose

In the title molecule, C8H15NO6, the pyranose ring adopts the usual 4C1(D) conformation and the N-acetyl group exists in the Z-anti conformation. The orientation of the primary alcohol group is gauche.

Direct preparation of N-glycosidic bond-linked nonionic carbohydrate-based surfactant (NICBS) via ritter reaction

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The reaction of unprotected sugar hydroxylamines and oximes with α-ketoacids leads to the chemoselective formation of glycosyl amides following the decarboxylative condensation pathway of Bode's ketoacid hydroxylamine (KAHA) ligation. Sugar oximes with gl

Method of producing an amide

The present invention discloses a new method for synthesizing an amide based on a fundamental mechanistic revision of the reaction of thio acids and organic azides. Moreover, the application of this method to the selective preparation of several classes of complex amides in nonpolar and polar solvents, including water, is provided.

RuCl3-promoted amide formation from azides and thioacids

Described here is the Ru(III)-promoted amide formation from azides and thioacids, which were shown not to form amides at room temperature in the absence of ruthenium. We belive that a complex formed by Ru(III) increases the reactivity of thiocarbonyl species and therefore reaction with azides occurs at room temperature, even when less reactive (electron rich and/or sterically hindered) azides are employed.

The reaction of thio acids with azides: A new mechanism and new synthetic applications

A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides that are difficult to access using conventional methods. The reaction is chemoselective, effective for unprotected substrates, and compatible with aprotic and protic solvents, including water. Copyright

The structure of glycosyl amides: A combined study by NMR spectroscopy, X-ray crystallography, and computational chemistry

The structure of N-formyl, N-acetyl-N-methyl, and N-acetyl glycosylamines has been studied by NMR spectroscopy in solution, single crystal X-ray diffractometry, and corroborated by PM3 semiempirical calculations. The results quite agree with an anti con formation around the glycosydic bond for these substances.

Improved synthesis of glycosylamines and a straightforward preparation of N-acylglycosylamines as carbohydrate-based detergents

D-Glucose, D-galactose, lactose, cellobiose, and maltose yield quantitatively the corresponding glycosylamine when treated at 42 deg C for 36 h with a commercial aqueous aolution of ammonia in the presence of one equivalent of ammonium hydrogen carbonate.After lyophilisation, the residue (i.e., the pure glucosylamine) was dissolved in a mixture of ethanol and water, and treated with acyl chlorides to afford in a few minutes N-acylglucosylamines.Micellar proporties of these amophiphilic derivatives were determined.Keywords: Glycosylamines; N-Acylglycosylamines; Non-ionic detergents; Carbohydrate-based detergents; Surfactants