Regioselective polycondensation of benzyl 2‐amino‐2‐deoxy‐α‐D‐glucopyranoside hydrochloride with carbon dioxide

Abstract

This paper reports the polycondensation of benzyl 2-amino-2-deoxy-a-o-glucopyranoside hydrochloride (1) with carbon dioxide using the triphenylphosphine/carbon tetrachlorideDBU system as a condensing agent to give poly(urethane) (2). The polycondensation of 1 with COz was carried out in DMF solvent in the presence of the condensing agent under CO, atmosphere. From the NMR and IR analyses of the product, the polymerization proceeded regioselectively to form 2. The molecular weight was estimated as 2000-3000 by GPC measurement after acetylation of 2, corresponding to DP = 5-8.ActaPolymer., 48, 310-313 (1997) Regioselective polycondensation of benzy12-amino-2-deoxy-a-o-glucopyranoside .. .Regioselective polycondensation of benzyl2-amino-2-deoxy-a-o-glucopyranoside . . .

Trends in polymer chemistry 1998

“…Furthermore, a new pathway to the synthesis of rod-coil-blockcopolymers has been presented in which extact end functionalized poly-p-phenylene is used as the rigid rod and polystyrene or polyethylenoxide as flexible, coiled segments [27].…”

Facile and direct synthesis of long-chain chitin from chitobiose via proton-assisted nonaqueous biocatalysis

“…13 [7]. Complete removal of the benzyl groups, however, was quite difficult while maintaining the N-acetyl groups at the C2 position [8]. Kobayashi and co-workers have reported the chemo-enzymatic synthesis of chitin with a high DP via an enzymatic ring-opening polyaddition of a chitobiose 2-oxazoline derivative by using chitinase in a phosphate buffer system at pH 10.6 [10].…”

“…* however it requires complicated multi-steps to guarantee strict regio/stereo-regulation, due to the presence of several equivalent hydroxyl groups and asymmetric carbon atoms in carbohydrates [5][6][7][8]. In view of this, many researchers have employed enzymatic and chemo-enzymatic methods to provide facile and efficient glycosynthetic procedures with regio/stereo-regulation [9][10][11][12].…”

Hyperbranched 5,6-glucan as reducing sugar ball

“…Thus, various types of dendrimers, star polymers, and hyperbranched polymers have been synthesized and their properties were compared to the linear analogues. 23,[33][34][35][36][37][38][39][40][41][42][43][44][45][46] easily than glycodendrimers and star-shaped glycopolymers. [71][72][73][74][75][76] Recently, we proposed that the ringopening multibranching polymerization of anhydro and dianhydro sugars as latent AB m -type monomers should be a convenient method of synthesizing hyperbranched glycopolymers with a novel spherical macromolecular architecture, [77][78][79][80][81][82][83] for example, the hyperbranched polysaccharides from the cationic polymerization of 1,6-anhydro--D-hexopyranose, the hyperbranched poly(2,5-anhydro-D-glucitol) from 1,2:5,6-dianhydro-D-mannitol, and the hyperbranched polytetritols of 1,4-anhydrotetritol and 2,3-anhydrotetritol.…”