219983-35-4

Upstream product

• 100-39-0 benzyl bromide 
• 3351-43-7 ethyl 2-methyl-5-(D-arabino-tetritol-1-yl)furan-3-carboxylate 

Downstream Products

• 442513-08-8 3-hydroxymethyl-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 
• 551937-27-0 3-chloromethyl-2-methyl-5-(1',2',3',4'-tetra-O-benzyl-D-arabino-tetritol-1'-yl)furan 

Relevant academic research and scientific papers

Oxidation of polyhydroxyalkyl-heterocycles by cerium (IV). A convenient route to pyrrole-2,5-dicarbaldehydes

The synthesis of 3-ethoxycarbonyl-2,5-diformylpyrrole (2) from 3- ethoxycarbonyl-2-methyl-5-D-(arabino-tetritol-l-yl)pyrrole (1) by oxidation with ceric ammonium nitrate is described. When the reaction was applied to related furan derivatives, ethyl (5S,6R,7R)-2-acetyl-5,6,7,8- tetrabenzyloxyoct-2-enoate (8) was obtained as an E/Z mixture.

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.