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Updated: May 21, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
A new protecting group and linker for uridine ureido nitrogen
1Pharmaceutical Sciences, College of Pharmacy, University of Tennessee Health Science Center, 881 Madison, Memphis, TN 38163, USA.
None:
(2,6-Dichloro-4-methoxyphenyl) (2,4,6-trichlorophenyl) methoxymethyl chloride [1, monomethoxydiphenylmethoxylmethyl chloroide (MDPM-Cl)] shows a significant relative stability and 1 reacts with uridine ureido nitrogen in the presence of DBU to form the corresponding protected uridine 8 in 95% yield. The MDPM-protected uridines are stable to a wide variety of conditions utilized for the synthesis of analogs of capuramycin and muraymycins. Significantly, the MDPM protecting group can conveniently be deprotected by using 30% TFA in CH(2)Cl(2). In addition, polymer-bound MDPM-Cl 23 is useful for immobilization of uridine derivatives.
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