Media type: E-Article Title: Synthesis of a new 2‐amino‐glycan, poly‐(1→6)‐α‐D‐mannosamine, by ring‐opening polymerization of 1,6‐anhydro‐mannosamine derivatives Contributor: Hattori, Kazuyuki; Yoshida, Takashi Published: Wiley, 2012 Published in: Journal of Polymer Science Part A: Polymer Chemistry, 50 (2012) 21, Seite 4524-4531 Language: English DOI: 10.1002/pola.26262 ISSN: 0887-624X; 1099-0518 Keywords: Materials Chemistry ; Organic Chemistry ; Polymers and Plastics Origination: Footnote: Description: <jats:title>Abstract</jats:title><jats:p>A stereoregular 2‐amino‐glycan composed of a mannosamine residue was prepared by ring‐opening polymerization of anhydro sugars. Two different monomers, 1,6‐anhydro‐2‐azido‐mannose derivative (<jats:bold>3</jats:bold>) and 1,6‐anhydro‐2‐(<jats:italic>N, N</jats:italic>‐dibenzylamino)‐mannose derivative (<jats:bold>6</jats:bold>), were synthesized and polymerized. Although <jats:bold>3</jats:bold> gave merely oligomers, <jats:bold>6</jats:bold> was promptly polymerized into high polymers of the number‐average molecular weight (<jats:italic>M</jats:italic><jats:sub>n</jats:sub>) of 2.3 × 10<jats:sup>4</jats:sup> to 2.9 × 10<jats:sup>4</jats:sup> with 1,6‐α stereoregularity. The differences of polymerizability of <jats:bold>3</jats:bold> and <jats:bold>6</jats:bold> from those of the corresponding glucose homologs were discussed. It was found that an <jats:italic>N</jats:italic>‐benzyl group is exceedingly suitable for protecting an amino group in the polymerization of anhydro sugars of a mannosamine type. The simultaneous removal of <jats:italic>O</jats:italic>‐ and <jats:italic>N</jats:italic>‐benzyl groups of the resulting polymers was achieved by using sodium in liquid ammonia to produce the first 2‐amino‐glycan, poly‐(1→6)‐α‐<jats:sc>D</jats:sc>‐mannosamine, having high molecular weight through ring‐opening polymerization of anhydro sugars.© 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012</jats:p>