Synthesis of oligosaccharide-branched ribofuranan by ring-opening polymerization of a new anhydroribo trisaccharide monomer.
A new anhydroribotrisaccharide monomer, A2B3LR (1), was synthesized and ROP was carried out to elucidate the polymerizability and to obtain oligosaccharide-branched polysaccharides with defined structures. The new trisaccharide monomer was found to be polymerized readily with BF(3) . OEt(2) as a catalyst at -40 degrees C to give a lactose-branched polymer. Copolymerization with ADBR gave the corresponding copolymers in good yields. After removal of protective benzyl groups, D-lactose-branched ribofuranans with free hydroxyl groups were obtained in good yields. The structure of polymers was analyzed by (1)H, 13C, and two-dimensional NMR measurements, suggesting that D-lactose-branched ribofuranans had (1 --> 5)-alpha stereoregularity.
Yoshida
Dai
D
Department of Bio and Environmental Chemistry, Kitami Institute of Technology, 165 Koen-cho, Kitami 090-8507, Japan. yoshida@chem.kitami-it.ac.jp
Han
Shuqin
S
Narita
Kei-Ichi
K
Hattori
Kazuyuki
K
Yoshida
Takashi
T
D000812:Anhydrides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*
D000812:Anhydrides; D009844:Oligosaccharides; D011108:Polymers