Activation of hydroxyl groups in sugars using bis(tributyltin) oxide: retention of the organotin residues to give biologically active products

Article abstract of DOI:10.1016/0022-328X(89)87165-7

Tributyltin ethoxide has been shown to react with cyclic anhydrides to give tributylstannyl ethyl esters of phthalic, maleic and succinic acids.Treatment of tris(tributylstannyl)-D-glucose with phthalic anhydride gave either the 1,6-di-O-phthalyl or the 6-O-phthalyl derivatives, respectively, depending on conditions, demonstrating that the the stannyl group can be used for activation and subsequently retained in the product.This synthetic procedure seems preferable to that in which phthalation precedes stannylation.