ABSTRACT
The benet of multivalent interactions over monovalent interactions in various branches of the life sciences has been well established.1 It is known as the cluster effect or dendritic effect.2 Pentaerythritol [1, tetrakis(hydroxymethyl)methane, 2,2-bis(hydroxymethyl)1,3-propanediol] is a scaffold widely used in the synthesis of glycoclusters and glycodendrimers. It can be derivatized to allow preparation of a
Experimental .......................................................................................................... 214 General Methods ............................................................................................... 214 Tetrakis(2-propynyloxymethyl)methane (Tetra-O-propargyl Pentaerythritol, 2) .............................................................................................. 214
Acknowledgment ................................................................................................... 215 References .............................................................................................................. 216
large variety of mono-, di-, tri-, or tetra-substituted derivatives.3,4 Full propargylation of 1 leads to tetrakis(2-propynyloxymethyl)methane (2). The latter is an important intermediate in making the rst generation of multivalent ligands, for example by CuI-catalyzed azide-alkyne 1,3-dipolar cycloaddition known as “click chemistry.”5,6 Compound 2 has been previously prepared and reported as both an amorphous7 and a crystalline8-10 substance. The compound has been fully characterized9 but we could not reproduce the best reported9 yield of 87%. According to the protocol described9 the reaction was conducted in DMSO as solvent without cooling to sub-ambient temperature. According to our experience, in order to obtain high yield of 2 the reaction has to be conducted at temperatures close to 0˚C, which the use of DMSO9 as solvent does not allow. Here we describe a reliable, high-yielding synthesis of 2.
