442513-09-9

Upstream product

• 3351-43-7 ethyl 2-methyl-5-(D-arabino-tetritol-1-yl)furan-3-carboxylate 
• 219983-35-4 3-ethoxycarbonyl-2-methyl-5-(1',2',3',4'-tetra-O-benzyl-D-arabino-tetritol-1-yl)furan 
• 100-39-0 benzyl bromide 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 442513-08-8 3-hydroxymethyl-2-methyl-5-(1',2',3',4'-tetra-O-benzyl-D-arabino-tetritol-1-yl)furan 

Relevant academic research and scientific papers

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.