Synthesis of chemically and functionally diverse scaffolds from pentaerythritol

Pentaerythritol (2,2-bis-hydroxymethyl-propane-1,3-diol) was converted into a series of mono-, di-, and trisubstituted derivatives, comprising allyl ethers and amino-alkyl ethers, by systematic chemical manipulation of the hydroxy groups. The remaining hydroxymethyl group in the case of the trisubstituted analog was functionalized with ether groups bearing terminal omega-carboxyl or omega-alkene groups. These derivatives are versatile templates and scaffolds for single, double, or triple substitution with appropriate ligands forming amides and esters, and allowing the attachment of the omega-alkene or omega-carboxyl group to solid support for combinatorial chemistry.