per-6-azido-per-6-deoxy-3^I-O-propargyl-β-cyclodextrin | 1415579-14-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: per-6-azido-per-6-deoxy-3^I-O-propargyl-β-cyclodextrin
• 英文别名: (1S,3R,5R,6S,8R,10R,11R,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5,10,15,20,25,30,35-heptakis(azidomethyl)-46-prop-2-ynoxy-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,47,48,49-tridecol
• CAS: 1415579-14-4
• 化学式: C₄₅H₆₅N₂₁O₂₈
• 分子量: 1348.14
• InChiKey: QHEHDZFZFYCQSS-HCHLQLBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  94
• 可旋转键数：
  16
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  502
• 氢给体数：
  13
• 氢受体数：
  42

反应信息

• 作为产物：
  描述：

  per-O-acetyl-per-6-azido-per-6-deoxy-3^I-O-propargyl-β-cyclodextrin 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以70%的产率得到per-6-azido-per-6-deoxy-3^I-O-propargyl-β-cyclodextrin
  参考文献：
  名称：

  Synthesis of 3I-O and 2I-O-monosubstituted derivatives of per-6-azido-β-cyclodextrin—potential molecular scaffolds

  摘要：

  Alkylation of per-6-azido-beta-cyclodextrin by a suitable electrophilic reagent (cinnamyl bromide or propargyl bromide) gave a mixture of 3(I)-O and 2(I)-O regioisomers. After peracetylation and chromatographic separation on silica gel, pure isomers were isolated. Oxidative cleavage of cinnamyl double bond afforded the corresponding formylmethyl and carboxymethyl derivatives. The prepared scaffold molecules are equipped with two types of reactive groups which have a potential to serve as points of attachment for various compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.09.003

文献信息

• Synthesis of 3I-O and 2I-O-monosubstituted derivatives of per-6-azido-β-cyclodextrin—potential molecular scaffolds
  作者：Martin Popr、Simona Hybelbauerová、Jindřich Jindřich

  DOI：10.1016/j.carres.2012.09.003

  日期：2012.11

  Alkylation of per-6-azido-beta-cyclodextrin by a suitable electrophilic reagent (cinnamyl bromide or propargyl bromide) gave a mixture of 3(I)-O and 2(I)-O regioisomers. After peracetylation and chromatographic separation on silica gel, pure isomers were isolated. Oxidative cleavage of cinnamyl double bond afforded the corresponding formylmethyl and carboxymethyl derivatives. The prepared scaffold molecules are equipped with two types of reactive groups which have a potential to serve as points of attachment for various compounds. (C) 2012 Elsevier Ltd. All rights reserved.