ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside | 153062-24-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
• 英文别名: [(4aR,6S,7R,8S,8aR)-6-ethylsulfanyl-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] acetate
• CAS: 153062-24-9
• 化学式: C₂₄H₂₈O₆S
• 分子量: 444.549
• InChiKey: WREZGOLGUDWSGX-IHRCBTOASA-N

物化性质

• 沸点：
  569.1±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 甲醇 、 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 Angstroems MS 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 、 乙酸酐 为溶剂， 反应 29.33h， 生成
  参考文献：
  名称：

  Synthesis of the Tetrasaccharide Repeating Unit of the Antigen from Escherichia coli O126 as Its Methyl Glycoside

  摘要：

  The tetrasaccharide repeating unit (17) of the antigen from E, coli O126 has been synthesized as its methyl glycoside by sequential addition of monosaccharide derivatives. The formation of the beta-mannosidic linkage was achieved by Swern oxidation of the glucose derivative followed by reduction of the product with sodium borohydride.

  DOI：

  10.1080/07328309808001883
• 作为产物：
  描述：

  乙基 4,6-O-亚苄基-beta-D-硫代吡喃葡萄糖苷 在 二正丁基氧化锡 、 cesium fluoride 作用下， 以 吡啶 为溶剂， 反应 21.0h， 生成 ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the Tetrasaccharide Repeating Unit of the Antigen from Escherichia coli O126 as Its Methyl Glycoside

  摘要：

  The tetrasaccharide repeating unit (17) of the antigen from E, coli O126 has been synthesized as its methyl glycoside by sequential addition of monosaccharide derivatives. The formation of the beta-mannosidic linkage was achieved by Swern oxidation of the glucose derivative followed by reduction of the product with sodium borohydride.

  DOI：

  10.1080/07328309808001883

文献信息

• Anthrax carbohydrates, synthesis and uses thereof
  申请人：UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.

  公开号：US09310366B2

  公开（公告）日：2016-04-12

  The present invention presents the isolation, characterization and synthesis of oligosaccharides of Bacillus anthracis. Also presented are antibodies that bind to such saccharide moieties and various methods of use for such saccharide moieties and antibodies.

  本发明提供了炭疽芽孢杆菌寡糖的分离、表征和合成。还提供了结合到这种糖基团的抗体，以及针对这种糖基团和抗体的各种使用方法。
• Synthesis of A Di-and a Trisaccharide Related to the Antigen from<i>Klebsiella</i>Type 43
  作者：Sumita Sarbajna、Anup K. Misra、Nirmolendu Roy

  DOI：10.1080/00397919808004824

  日期：1998.7

  Starting from D-galactose, D-mannose and D-glucose methyl alpha-D-galactopyranosyl-(1-->3)-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranoside and allyl beta-D-mannopyranosyl-(1-->4)-beta-D-glucopyranosyl uronate were synthesised in a highly stereoselective manner.
• HEPARAN SULFATE SYNTHESIS
  申请人：BOONS Geert-Jan

  公开号：US20120142560A1

  公开（公告）日：2012-06-07

  The invention provides an efficient modular chemical synthesis for heparan sulfate oligosaccharides based on orthogonal protection strategies. Modular disaccharide building blocks, themselves the product of a novel combinatorial synthesis, are combined in numerous ways to produce a range of oligosaccharides.