ol802229b_si_001.pdf (6.7 MB)

Protecting-Group-Based Colorimetric Monitoring of Fluorous-Phase and Solid-Phase Synthesis of Oligoglucosamines

Download (6.7 MB)
journal contribution
posted on 04.12.2008, 00:00 by Kwang-Seuk Ko, Gisun Park, Yang Yu, Nicola L. Pohl
A new hydroxyl protecting group, nitrophthalimidobutyric (NPB) acid, has been synthesized in one solvent-free step for colorimetric monitoring of reaction cycles upon its facile removal with hydrazine acetate in the solid-phase and fluorous-phase syntheses of antigenic oligoglucosamines associated with infectious Staphylococcus aureus. The NPB group serves as a convenient hydroxyl protecting group that is stable to the basic conditions required for the synthesis of the common trichloroacetimidate protecting groups, the strongly acidic conditions used in glycosylation reactions, as well as conditions commonly used to remove silicon-based protecting groups.