5-hydroxy-3-oxa-pentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 126765-18-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-hydroxy-3-oxa-pentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: 2-[(2-hydroxyethyl)oxy]ethyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-(2-hydroxyethoxy)ethoxy]oxan-2-yl]methyl acetate
• CAS: 126765-18-2
• 化学式: C₁₈H₂₈O₁₂
• 分子量: 436.413
• InChiKey: FTAKABYCPWTDMQ-UYTYNIKBSA-N

物化性质

• 熔点：
  92-93 °C
• 沸点：
  509.5±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5-hydroxy-3-oxa-pentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 吡啶 、 sodium azide 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 80.0h， 生成 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(2-azidoethoxy)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Szurmai, Zoltan; Szabo, Lajos; Liptak, Andras, Acta Chimica Hungarica, 1989, vol. 126, # 2, p. 259 - 270

  摘要：

  DOI：
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 氢溴酸 、 溶剂黄146 、 silver carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 5-hydroxy-3-oxa-pentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  [EN] GLUCOSE SENSITIVE INSULIN DERIVATIVES AND USES THEREOF
  [FR] DÉRIVÉS D'INSULINE SENSIBLES AU GLUCOSE ET LEURS UTILISATIONS

  摘要：

  The present invention relates to novel insulin derivatives and their use in the treatment or prevention of medical conditions relating to diabetes. The insulin derivatives are glucose sensitive and display glucose-sensitive insulin receptor binding. The invention also relates to novel intermediates. Finally, the invention provides a pharmaceutical composition comprising the insulin derivatives of the invention and the use of such a composition in the treatment or prevention of medical conditions relating to diabetes.

  公开号：

  WO2023144240A1

文献信息

• PHOSPHORAMIDITE BUILDING BLOCKS FOR SUGAR-CONJUGATED OLIGONUCLEOTIDES
  申请人：AM CHEMICALS LLC

  公开号：US20160083414A1

  公开（公告）日：2016-03-24

  Novel nucleoside phosphoramidite building blocks for preparation of synthetic oligonucleotides containing at least one phosphotriester linkage conjugated to a monosaccharide and synthetic processes for making the same are disclosed. Furthermore, oligomeric compounds are prepared using said building blocks, preferably followed by removal of protecting groups to provide monosaccharide-conjugated oligonucleotides.

  揭示了用于制备含至少一种磷酸三酯键连接的寡核苷酸的合成寡核苷酸的新型核苷酸磷酰胺酯构建模块，其与单糖偶联，并公开了制备这些构建模块的合成过程。此外，使用这些构建模块制备寡聚合物化合物，最好是在去除保护基之后，以提供单糖偶联的寡核苷酸。
• Separation of proteins using supramolecular gel electrophoresis
  作者：Sachiyo Yamamichi、Yuki Jinno、Nana Haraya、Takanori Oyoshi、Hideyuki Tomitori、Keiko Kashiwagi、Masamichi Yamanaka

  DOI：10.1039/c1cc13826j

  日期：——

  An amphiphilic low-molecular-weight hydrogelator 1 was synthesized. A tris-glycine-SDS solution gel of 1 was applied for electrophoresis to separate proteins. Centrifugation of a mixture of protein and a hydrogel of 1 enabled the recovery of protein. Various combinations of proteins were applied for supramolecular gel electrophoresis (SUGE), and remarkably poor mobility for small proteins (<45 kDa) was found.

  合成了一种两亲性低分子量水凝胶剂1。将1的三甘氨酸-SDS溶液凝胶用于电泳以分离蛋白质。将蛋白质与水凝胶1的混合物离心，可以回收蛋白质。对超分子凝胶电泳（SUGE）应用了各种蛋白质组合，发现小蛋白质（<45 kDa）移动性极差。
• Chemical Stimuli-Responsive Supramolecular Hydrogel from Amphiphilic Tris-Urea
  作者：Masamichi Yamanaka、Nana Haraya、Sachiyo Yamamichi

  DOI：10.1002/asia.201000791

  日期：2011.4.4

  An‐gel interceptor: An amphiphilic low‐molecular‐weight hydrogelator 1 was synthesized. Gel‐to‐sol phase‐transitions were caused by adding a surplus of ConA to a hydrogel of 1 or by adding anions. This anion response allows for naked‐eye detection of the hardness of mineral water.

  An-gel拦截器：合成了两亲性低分子量水凝胶剂1。凝胶到溶胶的相变是通过向1的水凝胶中添加过量的ConA或添加阴离子引起的。这种阴离子反应可以肉眼检测矿泉水的硬度。
• Phosphoramidite building blocks for sugar-conjugated oligonucleotides
  申请人：AM CHEMICALS LLC

  公开号：US10087208B2

  公开（公告）日：2018-10-02

  Novel nucleoside phosphoramidite building blocks for preparation of synthetic oligonucleotides containing at least one phosphotriester linkage conjugated to a monosaccharide and synthetic processes for making the same are disclosed. Furthermore, oligomeric compounds are prepared using said building blocks, preferably followed by removal of protecting groups to provide monosaccharide-conjugated oligonucleotides.

  本发明公开了用于制备合成寡核苷酸的新型核苷亚磷酰胺构筑基块，该核苷亚磷酰胺构筑基块含有至少一个与单糖共轭的磷酸三酯连接，并公开了制备该核苷亚磷酰胺构筑基块的合成工艺。此外，还利用所述构筑基块制备了寡聚化合物，最好随后去除保护基团，以提供单糖共轭寡核苷酸。
• Study on glycosylated prodrugs of toxoflavins for antibody-directed enzyme tumor therapy
  作者：Shusheng Wang、Dan Liu、Xu Zhang、Shengyu Li、Yongxu Sun、Jia Li、Yifa Zhou、Liping Zhang

  DOI：10.1016/j.carres.2007.03.006

  日期：2007.7

  Eight novel toxoflavin glycosides, which are potential prodrugs in antibody directed enzyme prodrug therapy (ADEPT), were synthesized. The structures of all toxoflavin glycosides were characterized by C-13 NMR spectroscopy, elemental analysis, and MS. Their enzymatic hydrolysis activities were tested against P-glucosidase (EC.3.2.1.21). (C) 2007 Elsevier Ltd. All rights reserved.