263382-45-2

Basic information

• Product Name: 3-O-acetyl-1,2-O-isopropylidene-4-O-toluene-p-sulfonyl-β-D-fructopyranose
• CAS NO: 263382-45-2
• Molecular Weight: 416.449
• Mol File: 263382-45-2.mol

Chemical Properties

• CAS DataBase Reference: 3-O-acetyl-1,2-O-isopropylidene-4-O-toluene-p-sulfonyl-β-D-fructopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-acetyl-1,2-O-isopropylidene-4-O-toluene-p-sulfonyl-β-D-fructopyranose(263382-45-2)
• EPA Substance Registry System: 3-O-acetyl-1,2-O-isopropylidene-4-O-toluene-p-sulfonyl-β-D-fructopyranose(263382-45-2)

Safety Data

• Hazardous Substances Data: 263382-45-2(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 263382-46-3 3,5-di-O-acetyl-1,2-O-isopropylidene-4-O-toluene-p-sulfonyl-β-D-fructopyranose 

Relevant articles and documents

3,4-Anhydro-1,2-O-isopropylidene-β-D-tagatopyranose and 4,5-anhydro- 1,2-O-isopropylidene-β-D-fructopyranose

3,4-Anhydro-1,2-O-isopropylidene-β-D-tagatopyranose (8) and 4,5- anhydro-1,2-O-isopropylidene-β-D-fructopyranose (10) have been prepared by treatment of 3,5-di-O-acetyl-1,2-O-isopropylidene-4-O-toluene-p-sulfonyl-β- D-fructopyranose with methanolic sodium methoxide. The structures of 8 and 10 were assigned by 1H and 13C NMR spectroscopy and that of 10 by X-ray crystallography; both exist in half-chair conformations. Compounds 8 and 10 interconvert in aqueous sodium hydroxide, giving a ratio of 1:2 at equilibrium. The monoacetates of 8 and 10 (5-O-acetyl-3,4-anhydro-1,2-O- isopropylidene-β-D-tagatopyranose and 3-O-acetyl-4,5-anhydro-1,2-O- isopropylidene-β-D-fructopyranose) undergo stereospecific epoxide ring opening in 80% acetic acid to give mainly the axial monoacetates 5-O-acetyl- 1,2-O-isopropylidene-β-D-fructopyranose and 4-O-acetyl-1,2-O-isopropylidene- β-D-tagatopyranose, respectively. (C) 2000 Elsevier Science Ltd.