A 4-(dimethylamino)pyridine (DMAP)-promoted polycondensation was developed as an efficient polymerization method to synthesize high molecular weight poly(ortho esters). A di-functional AB-monomer, 2,3,4-tri-O-acetyl-a-D-glucopyranosyl bromide was synthesized and subjected to DMAP-promoted polycondensation, which produced poly(ortho esters) with molecular weights up to 8.0 kDa. The NMR analyses indicate that the polymerization is highly chemoselective with exclusive formation of orthoester linkages between each sugar units.  The chain-end functionalization was achieved using alkynyl groups. Finally, poly(ethylene glycol) (PEG) was added to yield di-block polymer through Click chemistry.

Synthesis of high molecular weight sugar poly(ortho esters) through DMAP-promoted polycondensation

247th National Meeting (2014)

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