18685-22-8

Basic information

• Product Name: 1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• Synonyms: 1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• CAS NO: 18685-22-8
• Molecular Weight: 1063.3
• Mol File: 18685-22-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside(18685-22-8)
• EPA Substance Registry System: 1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside(18685-22-8)

Safety Data

• Hazardous Substances Data: 18685-22-8(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 57-50-1 Sucrose 
• 28697-76-9 1,3,4,6-tetra-O-benzyl-D-fructofuranosyl acetate 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 80763-60-6 ethyl 2-thio-α-D-fructofuranoside 
• 174848-29-4 1,3,4,6-tetra-O-benzoyl-D-fructofuranosyl acetate 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 80763-70-8 ethyl tetra-O-benzyl-2-thio-α-D-fructofuranoside 
• 100-44-7 benzyl chloride 

Downstream Products

• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 1206803-49-7 1,3,4-tri-O-benzyl-6-O-triethyl-silyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 1206803-50-0 1,3,4-tri-O-benzyl-6-O-triethyl-silyl-β-D-fructofuranosyl 2,3,4-tri-O-benzyl-6-O-triethyl-silyl-α-D-glucopyranoside 
• 59531-24-7 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 92691-79-7 1,3,4,6-tetra-O-benzyl-α-D-fructofuranose 
• 92691-80-0 1,3,4,6-tetra-O-benzyl-β-D-fructofuranose 
• 77887-11-7 1,3,4,6,1',3',4',6'-octa-O-benzyl-β-D-fructofuranosyl-β-D-fructofuranoside 
• 77887-11-7 1,3,4,6,1',3',4',6'-octa-O-benzyl-α-D-fructofuranosyl-α-D-fructofuranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 86049-38-9 5-((benzyloxy)methyl)-furan-2-carbaldehyde 

Relevant articles and documents

A highly efficient d-fructofuranosylation catalyzed by scandium(III) triflate

This Letter describes a highly efficient d-fructofuranosylation catalyzed by scandium(III) triflate. The benzylated and benzoylated d-fructofuranosyl acetate derivatives worked as good reactive donors in the presence of only 5 mol % scandium(III) triflate

Preparation of partially benzylated mono-, di-, and trisaccharides by selective cleavage of the β-fructofuranosidic linkage in fully benzylated sucrose and sucrose-related oligosaccharides under acidic conditions

Several partially benzylated mono-, di-, and trisaccharides having an anomeric hydroxyl group were successfully prepared by selective cleavage of the β-fructofuranosidic linkage in fully benzylated sucrose and sucrose-related oligosaccharides derived from lactosucrose, raffinose, melezitose, stachyose, and nystose under acidic conditions using 1:10 75% aqueous sulfuric acid-dioxane at room temperature for 1 h.

Synthesis of D-fructofuranosides using thioglycosides as glycosyl donors

Benzylated and benzoylated ethyl thioglycosides of D-fructofuranose have been synthesized and tested as glycosyl donors in couplings to various primary and secondary carbohydrate acceptors. Treatment of 2-O-acetyl-1,3,4,6-tetra-O-benzoyl-D-fructofuranose with ethyl mercaptan in a BF3·-etherate-promoted reaction gave the benzoylated ethyl 2-thio-α,β-D-fructofuranosides, which after deacylation and benzylation afforded the benzylated derivatives. These thiofructofuranosides, using dimethyl(methylthio)sulfonium triflate (DMTST) or N-iodosuccinimide as promoter, were found to be excellent donors, which gave disaccharide coupling products in quantitative or almost quantitative yields with all tested acceptors, yields rarely found in oligosaccharide synthesis. The benzoylated donors gave only α-linked fructofuranosides, due to participation of the 3-O-benzoyl group, whereas the benzylated donors gave α/β-mixtures.