Synthesis of branched polysaccharides by polymerization of 6-O-t-butyldimethylsilyl-D-glucal through stereoregular haloglycosylation

Jun-Ichi Kadokawa; Masao Yamamoto; Hideyuki Tagaya; Koji Chiba

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Synthesis of branched polysaccharides by polymerization of 6-O-t-butyldimethylsilyl-D-glucal through stereoregular haloglycosylation

机译：通过立体规则的卤代糖基化反应聚合6-O-叔丁基二甲基甲硅烷基-D-葡糖醛来合成支链多糖

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In this letter, we report synthesis of branched polysaccharide 2 by glycosylation of glucal-type monomer 1 with two free hydroxy groups at position 3 and 4. Monomer 1 polymerized with N-halosuccinimide promoter in acetonitrile solvent at room temperature - 50 ℃. The product was isolated as a petroleum ether insoluble fraction. The structure was determined by ~1H and ~(13)C NMR spectra as well as elemental analysis to be a polysaccharide consisting of 2-halo-2-deoxy-α-D-mannoside units, indicating that the polymerization proceeded via stereoregular glycosylation manner. The molecular weights determined by GPC with DMF were 3300 - 4000. The degree of branching was estimated by the NMR data of the product from the reaction of 2 with 3,5-dinitrobenzoyl chloride.

机译：在这封信中，我们报道了通过在3和4位上带有两个游离羟基的葡糖型单体1的糖基化来合成支链多糖2。单体1与N-卤代琥珀酰亚胺促进剂在乙腈溶剂中于室温-50℃聚合。分离出产物，为石油醚不溶级分。通过〜1H和〜（13）C NMR光谱以及元素分析确定结构为由2-卤-2-脱氧-α-D-甘露糖苷单元组成的多糖，表明聚合反应通过立体有规糖基化方式进行。由GPC用DMF测定的分子量为3300-4000。通过2与3,5-二硝基苯甲酰氯反应所得产物的NMR数据估算支化度。

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来源
《Carbohydrate letters》 |2001年第2期|共5页
作者
Jun-Ichi Kadokawa; Masao Yamamoto; Hideyuki Tagaya; Koji Chiba;
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正文语种 eng
中图分类有机化学;
关键词
branched polysaccharide; haloglycosylation; 2-halo-2-deoxy-α-D-mannoside;

机译：分支多糖;糖基化;2-卤-2-脱氧-α-D-甘露糖苷;

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1. Synthesis of branched polysaccharides by polymerization of 6-O-t-butyldimethylsilyl-D-glucal through stereoregular haloglycosylation [J] . Jun-Ichi Kadokawa, Masao Yamamoto, Hideyuki Tagaya, Carbohydrate letters . 2001,第2期

机译：通过立体规则的卤代糖基化反应聚合6-O-叔丁基二甲基甲硅烷基-D-葡糖醛来合成支链多糖
2. Synthesis of branched polymers by means of living anionic polymerization. 13. Synthesis of well-defined star-branched polymers via an iterative approach using living anionic polymers [J] . Hirao A., Higashihara T. Macromolecules . 2002,第19期

机译：通过活性阴离子聚合合成支化聚合物。 13.使用活性阴离子聚合物通过迭代方法合成定义明确的星形支化聚合物
3. Biologically Active Branched Polysaccharide Mimetics: Synthesis via Ring-Opening Polymerization of a Maltose-Based beta-Lactam [J] . Xiao Ruiqing, Zeng Jialiu, Grinstaff Mark W. ACS Macro Letters . 2018,第7期

机译：生物活性支链多糖模拟物：通过麦芽糖的β-内酰胺的开环聚合合成
4. Synthesis of branched polysaccharides by ring-opening polymerization of anhydro-oligosaccharide derivatives [C] . Takashi YOSHIDA, Kazuyuki HATTORI, Kei-ichi NARITA 11th International Symposium of Fine Chemistry and Functional Polymers Jul 28-31, 2001 Hailar, Inner Mongolia, P.R. China . 2001

机译：通过脱水寡糖衍生物的开环聚合合成支链多糖
5. New high-activity zinc(II)-based catalysts for ring-opening polymerization: Synthesis of stereoregular biodegradable polymers. [D] . Cheng, Ming. 2000

机译：用于开环聚合的新型高活性锌（II）基催化剂：立体有规可生物降解聚合物的合成。
6. Biosynthesis of the Escherichia coli K5 polysaccharide a representative of group II capsular polysaccharides: polymerization in vitro and characterization of the product. [O] . A Finke, D Bronner, A V Nikolaev, 1991

机译：大肠杆菌K5多糖（II类荚膜多糖的代表）的生物合成：体外聚合和产物表征。
7. Synthesis of New Branched Polysaccharide by Ring-Opening Polymerization of Anhydro-Deoxyglucose Derivative and the Subsequent Glycosylation of the Polysaccharide Derivative. [O] . Kenichi HATANAKA, Sanae OHTA, Maria Carmelita KASUYA, 1998

机译：红氧化氧氧氧氧化物衍生物的开环聚合对新的支化多糖的合成及多糖衍生物的随后糖基化。
8. Stereospecificity in the Free Radical Polymerization of Vinyl Acetate (Part Ⅰ). Synthesis of Model Branched Polymers (Part Ⅱ). Thermally Stable Polymers Containing the Triazine Ring (Part Ⅲ). Models of Stereoregular Polymers (Part Ⅳ) [R] . Barbara Boteler, T. G. Fox, Franz Wenger 1959

机译：乙酸乙烯酯自由基聚合的立体特异性（Ⅰ）。模型支化聚合物的合成（Ⅱ）。含三嗪环的热稳定聚合物（第Ⅲ部分）。立体聚合物模型（第四部分）

Synthesis of branched polysaccharides by polymerization of 6-O-t-butyldimethylsilyl-D-glucal through stereoregular haloglycosylation

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