초록 ▼

The present invention involves the synthetic conversion of pyridinoline (PYD) to deoxypyridinoline (DPD) via an intermediate ester which is subsequently cleaved. The transformation of PYD into a xanthate-type ester intermediate facilitates the subsequent removal of the substituted hydroxyl functiona

The present invention involves the synthetic conversion of pyridinoline (PYD) to deoxypyridinoline (DPD) via an intermediate ester which is subsequently cleaved. The transformation of PYD into a xanthate-type ester intermediate facilitates the subsequent removal of the substituted hydroxyl functionality thus providing the desired DPD. The method provides a new chemical pathway for the preparation of DPD, resulting in significantly increased yields as compared to traditional methods of product isolation.

대표청구항 ▼

[ What is claimed is:] [1.] A method for the chemical conversion of pyridinoline to deoxypyridinoline which comprises the steps of:a) reacting pyridinoline with an alkali metal hydride in an appropriate solvent with heating wherein the equivalents ratio of hydride to pyridinoline is from about 1 to

[ What is claimed is:] [1.] A method for the chemical conversion of pyridinoline to deoxypyridinoline which comprises the steps of:a) reacting pyridinoline with an alkali metal hydride in an appropriate solvent with heating wherein the equivalents ratio of hydride to pyridinoline is from about 1 to 5 to obtain deprotonated pyridinoline;b) reacting the deprotonated pyridinoline with an excess of carbon disulfide to obtain an intermediate dithiocarbonate;c) reacting the intermediate dithiocarbonate with an alkyl iodide to obtain the corresponding S-alkyl dithiocarbonate;d) cooling the reaction followed by adding an aqueous acid to the reaction to quench the S-alkyl dithiocarbonate; ande) reacting the S-alkyl dithiocarbonate with an alkyl tin hydride to obtain deoxypyridinoline.