1422345-67-2Relevant academic research and scientific papers
Synthesis of a new 2-amino-glycan, poly-(1→6)-α- D -mannosamine, by ring-opening polymerization of 1,6-anhydro-mannosamine derivatives
Hattori, Kazuyuki,Yoshida, Takashi
, p. 4524 - 4531,8 (2020/09/14)
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 (3) and 1,6-anhydro-2-(N, N-dibenzylamino)-mannose derivative (6), were synthesized and polymerized. Although 3 gave merely oligomers, 6 was promptly polymerized into high polymers of the number-average molecular weight (Mn) of 2.3 × 10 4 to 2.9 × 104 with 1,6-α stereoregularity. The differences of polymerizability of 3 and 6 from those of the corresponding glucose homologs were discussed. It was found that an N-benzyl group is exceedingly suitable for protecting an amino group in the polymerization of anhydro sugars of a mannosamine type. The simultaneous removal of O- and N-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-D- mannosamine, having high molecular weight through ring-opening polymerization of anhydro sugars.
