38982-46-6

Basic information

• Product Name: Anhydrofructose
• Synonyms: Anhydrofructose
• CAS NO: 38982-46-6
• Molecular Formula: C₆H₁₀O₅
• Molecular Weight: 162.14
• Mol File: 38982-46-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Anhydrofructose(CAS DataBase Reference)
• NIST Chemistry Reference: Anhydrofructose(38982-46-6)
• EPA Substance Registry System: Anhydrofructose(38982-46-6)

Safety Data

• Hazardous Substances Data: 38982-46-6(Hazardous Substances Data)

Upstream product

• 57-50-1 Sucrose 
• 100-51-6 benzyl alcohol 
• 99042-47-4 2'-chloroethyl 1,3,4,5-tetra-O-acetyl-β-D-fructopyranoside 
• 1053626-36-0 phenyl 2-thio-β-D-fructopyranoside 
• 108-95-2 phenol 
• 71-36-3 butan-1-ol 
• 75-65-0 tert-butyl alcohol 
• 67-63-0 isopropyl alcohol 
• 150-76-5 4-methoxy-phenol 
• 64-17-5 ethanol 
• 106-44-5 p-cresol 
• 67-56-1 methanol 
• 67831-76-9 1,3,4-Tri-O-acetyl-2,6-anhydro-β-D-fructofuranose 
• 2280-44-6 D-Glucose 

Downstream Products

• 1053268-51-1 2,6-anhydro-1,3,4-tri-O-benzyl-β-D-fructofuranose 

Relevant articles and documents

Br?nsted acidity of ceric ammonium nitrate in anhydrous DMF. the role of salt and solvent in sucrose cleavage

The generation of an unexpected Br?nsted acidity in anhydrous DMF at 50°C was evidenced by NMR measurements during the investigation on the course of sucrose cleavage by ceric ammonium nitrate (CAN). The formation of a nitrooxy derivative of DMF by reaction with CAN is responsible for this acidity. The reactivity of CAN at 50°C with several solvents was evaluated by voltammetric and potentiometric measurements. The possible release of protons from these reactions, particularly when aqueous solvent mixtures are used, should always be taken into account in the mechanistic interpretation of CAN synthetic applications.

New synthesis of 2,6-anhydro-β-D-fructofuranoses, pivotal [2.2.1] bicyclic acetals for the conversion of D-fructose into 2,2,5-trisubstituted tetrahydrofurans

2,6-Anhydro-β-D-fructofuranose derivatives were prepared by a novel tin-promoted 2,5-cyclisation of phenyl 2-thio-β-D-fructopyranosides. They were regioselectively opened by allyltrimethylsilane in the presence of catalytic Sc(OTf)3 to give 2,2,5-trisubstituted tetrahydrofurans in high yields and major α-stereoselectivity.

Pyrolysis of inulin, glucose, and fructose

The pyrolytic behavior of inulin, a (2->1)-linked fructofuranan, is described.Parallel investigations of the pyrolysis of glucose and of fructose were conducted to supplement the inulin results and to aid comparison with previous results from glucans.Effects of neutral and basic additives are emphasized.As with glucans, the addition of such additives (especially basic) increases the yields of the one-, two-, and three-carbon products (as well as of hexosaccharinolactones), while generally decreasing the yields of anhydro sugar and furan derivatives.The former products include glycolaldehyde, acetol, dihydroxyacetone, acetic acid, formic acid, and lactic acid.Mechanistic speculations are made regarding the origins of these compounds, as well as of furan derivatives and saccharinic acid lactones.Parallels with alkaline degradation are considered.

Sucrochemistry: Part IX - An alternative preparation of 2,6-anhydro-β-D-fructofuranose

Synthesis of the title carbohydrate derivative, starting from easily available sucrose is described.

THERMOLYSIS OF SUCROSE IN THE PRESENCE OF ALCOHOLS. A NOVEL METHOD FOR THE SYNTHESIS OF D-FRUCTOFURANOSIDES

When sucrose is thermolyzed in the presence of alcohols, either neat or in dimethyl sulfoxide solution, the products are mainly D-glucose and the appropriate alkyl D-fructofuranosides.Conditions have been investigated for optimizing the yields of the latter products, with a view to utilization of the reaction as a synthetic method.Such sterically hindered alcohols as 2-methyl-2-propanol and three sterols did not readily take part in the reaction.Phenols appear to undergo the reaction, but the phenyl D-fructofuranosides are probably degraded subsequently, to give increased yields of 2,6-anhydro-D-fructofuranose.

THERMOLYSIS OF SUCROSE IN DIMETHYL SULPHOXIDE SOLUTION

The kinetics of thermolysis of sucrose in solution in anhydrous dimethyl sulphoxide have been studied.The reaction appears to be facilitated by intramolecular hydrogen-bonding and is inhibited by intermolecular hydrogen-bonding to water or alcohols.The thermolysis yields α-D-glucopyranose (which then anomerises) and the fructofuranosyl carbonium ion which can react with benzyl alcohol to yield benzyl α- and β-D-fructofuranosides.This fructosyl cation is probably also the precursor for the formation of 2,6-anhydrofructofuranose in the thermolysis of sucrose.