76880-54-1

Basic information

• Product Name: benzyl α-D-fructofuranoside
• Synonyms: benzyl α-D-fructofuranoside
• CAS NO: 76880-54-1
• Molecular Weight: 270.282
• Mol File: 76880-54-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: benzyl α-D-fructofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl α-D-fructofuranoside(76880-54-1)
• EPA Substance Registry System: benzyl α-D-fructofuranoside(76880-54-1)

Safety Data

• Hazardous Substances Data: 76880-54-1(Hazardous Substances Data)

Upstream product

• 13403-14-0 methyl α-D-fructofuranoside 
• 100-51-6 benzyl alcohol 
• 7647-01-0 hydrogenchloride 
• 57-48-7 D-Fructose 
• 67-56-1 methanol 
• 15219-29-1 benzyl β-D-fructopyranoside 
• 57-50-1 Sucrose 

Downstream Products

• 13403-14-0 methyl α-D-fructofuranoside 
• 53416-07-2 β-D-fructopyranoside, ethyl 
• 1820-84-4 2-ethyl-β-D-fructofuranoside 
• 81024-99-9 ethyl α-D-fructofuranoside 
• 57-48-7 D-Fructose 
• 106182-88-1 1,6-di-O-(p-tolylsulfonyl)-D-fructose 
• 10225-44-2 benzyl-(tetra-O-acetyl-α-D-fructofuranoside) 

Relevant articles and documents

FORMATION AND EQUILIBRATION OF D-FRUCTOSIDES AND 2-THIO-D-FRUCTOSIDES IN ACIDIFIED DIMETHYL SULFOXYDE: SYNTHETIC AND MECHANISTIC ASPECTS

A kinetic study of the reaction of ketoses and ketosides under catalysis with very dilute acid to produce the ketosyl carbonium ion is reported, and the subsequent reaction of this ion with alcohol and thiol nucleophiles has been studied.The relative reactivity of D-fructoses and 2-thio-fructosides is discussed, and some tentative conclusions have been reached on the mechanism of their furanoside-pyranoside equilibration.The change in ring size in such systems probably proceeds via an anhydro-D-fructose intermediate, rather than an acyclic intermediate.The synthetic applications of the system have been explored, and it has been shown that both D-fructosides and 2-thio-D-fructosides may be synthesized in good yield.The D-fructofuranosides are best obtained from sucrose as the starting material, whereas the pyranosides are obtained from any readily available D-fructopyranoside (e.g., methyl β) by use of the desired alcohol or thiol, only the β anomers being obtained.Three new 2-thio-D-fructosides are reported.

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.