Ring-opening polymerization of new 3-O-branched 1, 6-anhydro glucopyranose di- and trisaccharide monomers.
作者： Chaolumen Bai , Davaanyam Budragchaa , Takashi Yoshida
DOI: 10.1016/J.CARRES.2017.04.017
关键词: Steric effects 、 Polymer chemistry 、 Chemistry 、 Ring-opening polymerization 、 Polysaccharide 、 Trisaccharide 、 Polymerization 、 Disaccharide 、 Monomer 、 Polymer
摘要: New 3-O-branched 1, 6-anhydro glucopyranose disaccharide monomers, 6-anhydro-2, 4-di-O- benzyl-3-O-(2′, 3′, 4′, 6'-tetra-O-benzyl-α-D-mannopyranosyl)- (LGM 6) and -glucopyranosyl)-β-D- (LGG 7), a trisaccharide monomer, 4-di-O-benzyl-3-O-α-(2′, 6′, 2″, 3″, 4″, 6″-hepta-O-benzyl- α-D-maltopyranosyl)-β-D-glucopyranose (LGMAL 8), were synthesized polymerized. It was found that the 3-O-branched1, monomers However, polymerizability lower than of 4-O-branched reported previously, monomer not polymerizable, probably due to steric hindrance branched bulky mono units at 3-O position in glucopyranose. Debenzylation resulting polymers gave 3-O-gluco- mannopyranosidic (1 → 6)-α-D-glucopyranans moderate yields. These results are first reports polymerization give polysaccharides.
sci-hub.se 参考文章(17)
Davaanyam Budragchaa, Shiming Bai, Taisei Kanamoto, Hideki Nakashima, Shuqin Han, Takashi Yoshida, Synthetic galactomannans with potent anti-HIV activity Carbohydrate Polymers. ,vol. 130, pp. 233- 242 ,(2015) , 10.1016/J.CARBPOL.2015.04.047
Conrad Schuerch, Synthesis and Polymerization of Anhydro Sugars Advances in Carbohydrate Chemistry and Biochemistry. ,vol. 39, pp. 157- 212 ,(1981) , 10.1016/S0065-2318(08)60206-1
Monika Poláková, Mattias U. Roslund, Filip S. Ekholm, Tiina Saloranta, Reko Leino, Synthesis of β-(1→2)-Linked Oligomannosides European Journal of Organic Chemistry. ,vol. 2009, pp. 870- 888 ,(2009) , 10.1002/EJOC.200801024
Arata Hagino, Seiichi Yoshida, Tetsuro Shinpuku, Kei Matsuzaki, Toshiyuki Uryu, Selective ring-opening polymerization of 1,4-anhydro-α-D-lyxopyranose derivatives and synthesis of stereoregular (1 → 5)-α-D-lyxofuranan Macromolecules. ,vol. 19, pp. 1- 7 ,(1981) , 10.1021/MA00155A001
Kazukiyo Kobayashi, Koji Nomura, Masahiko Okada, Chemical synthesis of a comb-shaped, branched stereoregular polysaccharide, 4-O-α-d-mannopyranosyl-(1 → 6)-α-d-mannopyranan Carbohydrate Research. ,vol. 242, pp. 161- 166 ,(1993) , 10.1016/0008-6215(93)80030-I
Tommy Iversen, David R. Bundle, Synthesis of the colitose determinant of Escherichiacoli O111 and 3,6-di-O-(α-D-galactopyranosyl)-α-D-glucopyranoside Canadian Journal of Chemistry. ,vol. 60, pp. 299- 303 ,(1982) , 10.1139/V82-045
Dai Yoshida, Shuqin Han, Kei-Ichi Narita, Kazuyuki Hattori, Takashi Yoshida, Synthesis of oligosaccharide-branched ribofuranan by ring-opening polymerization of a new anhydroribo trisaccharide monomer. Macromolecular Bioscience. ,vol. 9, pp. 687- 693 ,(2009) , 10.1002/MABI.200800316
B. Veruovic, C. Schuerch, The preparation of comb-shaped polysaccharides by polymerization of a maltose derivative Carbohydrate Research. ,vol. 14, pp. 199- 206 ,(1970) , 10.1016/S0008-6215(00)80487-5
Takashi Yoshida, Kotaro Endo, Synthesis of Branched Ribo‐Polysaccharides with Defined Structures by Ring‐Opening Polymerization of 1,4‐Anhydro Ribo‐Disaccharide Monomer Macromolecular Bioscience. ,vol. 1, pp. 298- 304 ,(2001) , 10.1002/1616-5195(20011001)1:7<298::AID-MABI298>3.0.CO;2-4
T Yoshida, Synthesis of polysaccharides having specific biological activities Progress in Polymer Science. ,vol. 26, pp. 379- 441 ,(2001) , 10.1016/S0079-6700(00)00045-9