Synthesis of Oligomeric and Polymeric Monosaccharides by Aldol Group‐Transfer Polymerization

Abstract

The enediolate 2‐phenyl‐1,3,2‐dioxaborole 1 reacts in a living polymerization with aldehydes to give oligomers and polymers of type 2 with defined molecular weights. These compounds can be converted into the polysaccharides 3, which can react further as macromers and telechelics to give even more complex polymers.

Amphiphilic Polymers from Long-Chain (Z)-2-Alkoxyvinyl Acetates

“…(Z)-2-Alkoxyvinyl acetates 5 are prepared by a retro-Diels-Alder technique, which allows a general approach to symmetrically and unsymmetrically (Z)-1,2-dioxy-substituted olefins. 6,7 Starting material is diol 1, which is easily accessible by Diels-Alder reaction of vinylenecarbonate with anthracene, followed by saponification of the carbonate ester. 8 Diol 1 is converted into cyclic acetals 2 by reaction with aldehydes or acetone.…”