138528-01-5

Basic information

• Product Name: 3,4,5-tri-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose
• Synonyms: 3,4,5-tri-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose
• CAS NO: 138528-01-5
• Molecular Weight: 490.596
• Mol File: 138528-01-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3,4,5-tri-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5-tri-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose(138528-01-5)
• EPA Substance Registry System: 3,4,5-tri-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose(138528-01-5)

Safety Data

• Hazardous Substances Data: 138528-01-5(Hazardous Substances Data)

Upstream product

• 25018-67-1 1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose 
• 7660-25-5 D-fructose 
• 100-39-0 benzyl bromide 
• 66900-93-4 1,2-O-isopropylidene-β-D-fructopyranose 

Downstream Products

• 785803-51-2 (8R,9R,10S)-8,9,10-Tris-benzyloxy-3,6-dioxa-1-aza-spiro[4.5]decane-2-thione 
• 880480-38-6 1-O-acetyl-3,4,5-tri-O-benzyl-β-D-fructopyranose 
• 327172-71-4 3,4,5-tri-O-benzyl-α-D-fructopyranose 3,4,5-tri-O-benzyl-β-D-fructopyranose 1,2':2,1'-dianhydride 

Relevant articles and documents

Synthesis of 1,2-anhydro-3,4,5-tri-O-benzyl-β-D-fructopyranose

A synthesis of the anomeric spiro-epoxide 15 from D-fructose, in 7 steps in an overall 13percent yield, is described.The key intermediate in the synthesis, 3,4,5-tri-O-benzyl-1-deoxy-1-iodo-β-D-fructopyranose (14), was prepared from the corresponding methyl fructopyranoside by reaction with the iodine-triphenylphosphine-imidazole reagent complex, followed by acid hydrolysis.Ring closure of the iodohydrin 14 was achieved under extremely mild conditions on treatment with silver(I) oxide in anhydrous THF.The 13C NMR spectrum of 15 exhibited a large upfield shift of the resonances assigned to C-1 and C-2, indicative of an oxirane ring involving these two carbon atoms.

Synthesis of di- and trisaccharides comprising D-fructopyranose with β2→1 glycosidic linkage using β-D-fructopyranosyl fluoride as the fructosyl donor

D-Fructose was converted into a stable, suitably protected fructosyl donor for iterative glycosylation, i.e., 1-O-acetyl-3,4,5-tri-O-benzyl-β-D-fructopyranosyl fluoride and a fructosyl acceptor, methoxymethyl 3,4,5-tri-O-benzyl-β-D-fructopyranoside in goo