442513-08-8

Basic information

• Product Name: 3-hydroxymethyl-2-methyl-5-(1',2',3',4'-tetra-O-benzyl-D-arabino-tetritol-1-yl)furan
• Synonyms: 3-hydroxymethyl-2-methyl-5-(1',2',3',4'-tetra-O-benzyl-D-arabino-tetritol-1-yl)furan
• CAS NO: 442513-08-8
• Molecular Weight: 592.732
• Mol File: 442513-08-8.mol

Chemical Properties

• CAS DataBase Reference: 3-hydroxymethyl-2-methyl-5-(1',2',3',4'-tetra-O-benzyl-D-arabino-tetritol-1-yl)furan(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxymethyl-2-methyl-5-(1',2',3',4'-tetra-O-benzyl-D-arabino-tetritol-1-yl)furan(442513-08-8)
• EPA Substance Registry System: 3-hydroxymethyl-2-methyl-5-(1',2',3',4'-tetra-O-benzyl-D-arabino-tetritol-1-yl)furan(442513-08-8)

Safety Data

• Hazardous Substances Data: 442513-08-8(Hazardous Substances Data)

Upstream product

• 3351-43-7 ethyl 2-methyl-5-(D-arabino-tetritol-1-yl)furan-3-carboxylate 
• 100-39-0 benzyl bromide 
• 219983-35-4 3-ethoxycarbonyl-2-methyl-5-(1',2',3',4'-tetra-O-benzyl-D-arabino-tetritol-1-yl)furan 

Downstream Products

• 551937-27-0 3-chloromethyl-2-methyl-5-(1',2',3',4'-tetra-O-benzyl-D-arabino-tetritol-1'-yl)furan 
• 442513-09-9 3-(tert-butyldiphenylsilyloxymethyl)-2-methyl-5-(1',2',3',4'-tetra-O-benzyl-D-arabino-tetritol-1-yl)furan 

Relevant articles and documents

Hetaryleneaminopolyols and hetarylenecarbopeptoids: A new type of glyco- and peptidomimetics. Syntheses and studies on solution conformation and dynamics

Ready access to a new class of oligomers has been demonstrated by the synthesis of hetaryleneaminopolyols and hetarylenecarbopeptoids using 3-hydroxymethyl-5-(4-amino-4-deoxy-D-arabinotetritol1-yl)-2-methylfuran and 5-(4-amino-4-deoxy-D-arabinotetritol-1-yl)-2-methyl-3-furoic acid as novel scaffolds. The conformational behavior of peptidomimetics 22, 23, 25, 26, and 36 have been analyzed by NMR spectroscopy and extensive molecular dynamics simulations. MD simulations using the GB/SA continuum solvent model for water and the MM3* force field provide a population distribution of conformers which satisfactorily agrees with the experimental NMR data for the torsional degrees of freedom of the molecule.

Reactivity of polyhydroxyalkyl-heterocycles towards Lewis acids

We report the reactivity of different polyhydroxyalkyl-heterocycles towards ceric ammonium nitrate (CAN) and ferric chloride. The behaviour of 2-methyl-5-(tetritol-1-yl)-pyrroles and -furans is different towards CAN oxidation. Pyrroles afford 2,5-diformylheterocycles, while furans give access to 1,4-dicarbonyl compounds containing three stereogenic centres. Ferric chloride promotes an intramolecular C-arylation reaction on O-benzylated-polyhydroxyalkyl furans, yielding an isochroman moiety, which is the basic skeleton of a variety of natural products.