28697-72-5

Basic information

• Product Name: 1,3,4,6-tetra-O-benzyl-α,β-D-fructofuranose
• Synonyms: 1,3,4,6-tetra-O-benzyl-α,β-D-fructofuranose
• CAS NO: 28697-72-5
• Molecular Weight: 540.656
• Mol File: 28697-72-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,3,4,6-tetra-O-benzyl-α,β-D-fructofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4,6-tetra-O-benzyl-α,β-D-fructofuranose(28697-72-5)
• EPA Substance Registry System: 1,3,4,6-tetra-O-benzyl-α,β-D-fructofuranose(28697-72-5)

Safety Data

• Hazardous Substances Data: 28697-72-5(Hazardous Substances Data)

Upstream product

• 14233-64-8 tri-O-benzyl-D-arabinolactone 
• 66222-28-4 (benzyloxymethyl)tributylstannane 
• 470-23-5 D-fructose 
• 100-44-7 benzyl chloride 
• 1038507-70-8 1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-glucopyranoside 
• 1038507-72-0 1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-glucopyranoside 

Downstream Products

• 92588-04-0 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester 
• 92587-98-9 2-S-acetyl-1,3,4,6-tetra-O-benzyl-2-thio-β-D-fructofuranose 
• 92587-97-8 2-S-acetyl-1,3,4,6-tetra-O-benzyl-2-thio-α-D-fructofuranose 
• 84635-46-1 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitroanilino)-α-D-glucopyranose 
• 84039-29-2 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitroanilino)-α-D-glucopyranosyl 1,3,4,6-tetra-O-benzyl-α-D-fructofuranoside 
• 84039-30-5 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranosyl 1,3,4,6-tetra-O-benzyl-β-D-fructofuranoside 
• 73488-63-8 3,4,6-tri-O-acetyl-2-(2,4-dinitroanilino)-2-deoxy-α-D-glucopyranosyl 1',3',4',6'-tetra-O-benzyl-β-D-fructofuranoside 
• 92691-82-2 2-O-acetyl-1,3,4,6-tetra-O-benzyl-β-D-fructofuranose 
• 92691-81-1 2-O-acetyl-1,3,4,6-tetra-O-benzyl-α,β-D-fructofuranose 
• 92588-04-0 1,3,4,6-tetra-O-benzyl-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranoside 

Relevant articles and documents

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.

L-Sucrose and process for producing same

L-sucrose or β-L-fructofuranosyl α-L-glucopyranoside--(I), the enantiomer of naturally occuring D-sucrose, which does not appear in nature has been synthesized and has been found to be sweet. It is unlikely that L-sucrose is metabolized in the manner of D-sucrose. In a preferred process for producing L-sucrose the key step is the condensation of 2,3,4,6-tetra-O-benzyl-α-L-glucopyranosyl chloride--(II) with 1,3,4,6-tetra-O-benzyl-L-fructofuranose--(III). Compound II is obtained from L-glucose by way of 2,3,4,6-tetra-O-benzyl-α-L-glucopyranose; and L-glucose is prepared from L-arabinose by nitromethane synthesis. Compound III is obtained by oxidation, with Jones reagent, of 1,3,4,6-tetra-O-benzyl-L-mannitol which, in turn, is prepared from L-mannose. The condensation product of II and III is catalytically debenzylated to produce L-sucrose.