tetra-O-acetyl-β-D-ribofuranose

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tetra-O-acetyl-β-D-ribofuranose
• 英文别名: propargyl gluconamide；(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxy-N-prop-2-ynylhexanamide
• 化学式: C₉H₁₅NO₆
• 分子量: 233.221
• InChiKey: IYRKSXOEDNAYKQ-OOJXKGFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  130
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tetra-O-acetyl-β-D-ribofuranose 、 2,3-O-isopropylidene-β-D-ribofuranosyl-1-azide 在 copper acetate monohydrate 、 sodium carbonate 、 sodium ascorbate 作用下， 以 水 为溶剂， 反应 2.0h， 以96%的产率得到N-(1-(2,3-O-isopropylidene-β-D-ribofuranosyl)-triazol-4-ylmethyl)-D-glucoamide
  参考文献：
  名称：

  Efficient Synthesis of a Water-Soluble Glucoamide Inhibitor Against Human Aldose Reductase by Click Chemistry

  摘要：

  While D-glucose is the natural substrate of aldose reductase (AR) in the polyol pathway, the K-m value of D-glucose against AR is large. A glucoamide 1 was designed as a tool to investigate whether AR has a strong affinity for the open form of D-glucose. Glucoamide 1 was synthesized in high yield by modification of the reaction condition for click chemistry. It was found that our modified condition was applicable for highly polar alkynes and gave coupling products in excellent yield (90% to 100%). Although weak inhibitory activity against AR was observed, kinetic studies showed that AR does not accept glucoamide 1 in its active site.

  DOI：

  10.1080/07328303.2013.816852
• 作为产物：
  描述：

  炔丙胺 、 葡萄糖酸内酯 在 吡啶 作用下， 反应 18.0h， 以97%的产率得到tetra-O-acetyl-β-D-ribofuranose
  参考文献：
  名称：

  使用点击化学可高效合成水溶性杯芳烃。

  摘要：

  [反应：见正文]通过叠氮化物和炔烃之间的Huisgen 1,3-偶极环加成反应，合成了几种水溶性杯[4]芳烃。阳离子，阴离子和非离子杯芳烃是由一种常见的叠氮基芳烃中间体制备的。叠氮基杯芳烃作为前体的性能优于炔基杯芳烃。通过（1）H NMR光谱研究水溶性杯芳烃的聚集行为。

  DOI：

  10.1021/ol047468h

文献信息

• Versatile, efficient derivatization of polysiloxanes via click technology
  作者：Ferdinand Gonzaga、Gilbert Yu、Michael A. Brook

  DOI：10.1039/b821788b

  日期：——

  Copper-catalyzed (click chemistry) or thermal 1,3-dipolar cycloadditions of molecular or polymeric azido-siloxanes with a broad range of alkynes (such as amino acids or carbohydrates) easily yield new conjugates that would be otherwise difficult, if not impossible, to prepare by traditional methodologies.

  分子或聚合物叠氮硅氧烷与多种炔类（如氨基酸或碳水化合物）在铜催化（点击化学）或热力作用下发生 1,3-二极环加成反应，很容易制备出新的共轭物，而这些共轭物用传统方法很难制备，甚至不可能制备。
• MULTI-ARM LINKERS FOR CONSTRUCTING PHARMACEUTICAL MOLECULES
  申请人：Immunwork Inc.

  公开号：US20180110872A1

  公开（公告）日：2018-04-26

  The present disclosure provides various molecular constructs having a targeting element and an effector element. Methods for treating various diseases using such molecular constructs are also disclosed.