3^A-azido-3^A-deoxy-β-cyclodextrin | 223639-29-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3^A-azido-3^A-deoxy-β-cyclodextrin
• 英文别名: mono-2-azido-2-deoxy-β-cyclodextrin；3^I-deoxy-3^I-azido-altro-β-cyclodextrin；(1S,3R,5R,6S,8S,10R,11S,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)-48-azido-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-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-36,37,38,39,40,41,42,43,44,45,46,47,49-tridecol
• CAS: 223639-29-0
• 化学式: C₄₂H₆₉N₃O₃₄
• 分子量: 1160.01
• InChiKey: QFTQCFFKDVYESN-FOUAGVGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13.5
• 重原子数：
  79
• 可旋转键数：
  8
• 环数：
  21.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  548
• 氢给体数：
  20
• 氢受体数：
  36

反应信息

• 作为反应物：
  描述：

  3^A-azido-3^A-deoxy-β-cyclodextrin 在 ammonium hydroxide 、 三苯基膦 作用下， 生成 3^A-amino-3^A-deoxy-β-cyclodextrin
  参考文献：
  名称：

  The Dependence of Catalytic Activities of Secondary Functional .BETA.-Cyclodextrins on Cavity Structures.

  摘要：

  由新型中间体3-氨基-3-脱氧-β-环糊精合成的具有非扭曲空腔的仲咪唑β-环糊精5在酯水解中表现出比其具有扭曲空腔的异构体6更高的催化活性，表明催化活性二级功能环糊精的活性取决于空腔结构。

  DOI：

  10.1248/cpb.47.588
• 作为产物：
  描述：

  C-3 monotosyl β-cyclodextrin 在 sodium azide 作用下， 以 水 为溶剂， 反应 72.0h， 以72%的产率得到3^A-azido-3^A-deoxy-β-cyclodextrin
  参考文献：
  名称：

  A reliable synthesis of 2- and 6-amino-β-cyclodextrin and permethylated-β-cyclodextrin

  摘要：

  A new, reliable method for the introduction of an amine group at positions 2 or 6 of beta-cyclodextrin and permethyl-beta-cyclodextrin is described. It involves selective tosylation followed by azide substitution and almost quantitative reduction with triphenylphosphine followed by hydrolysis of the phosphinimine intermediate. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.099

文献信息

• Functionalization of Cyclodextrins via Reactions of 2,3-Anhydrocyclodextrins
  作者：De-Qi Yuan、Tsutomu Tahara、Wen-Hua Chen、Yuji Okabe、Cheng Yang、Youichi Yagi、Yasuyoshi Nogami、Makoto Fukudome、Kahee Fujita

  DOI：10.1021/jo035229m

  日期：2003.11.1

  ring-opening products. By ameliorating the reaction condition, cyclodextrin olefin, diene, and triene derivatives are prepared in moderate to good yields. Reduction of per[6-(tert-butyldimethyl)silyl]-beta-cyclodextrin permannoepoxide with lithium aluminum hydride produces the per(3-deoxy)-beta-cyclomannin. All these chemically modified cyclodextrins are structurally well characterized and most of them are expected

  已经研究了3,2,3-脱水β-环糊精的三种类型的反应，即亲核开环，还原为2-烯吡喃糖和还原为3-脱氧吡喃糖，以区域和立体选择性地官能化β-环糊精的次表面。在用各种亲核试剂处理后，发现2，3-甘露环氧和2，3-丙氧基-β-环糊精都经历亲核开环反应，产生3-和2-修饰的环糊精衍生物。在每种情况下，3位比2位更容易接近。通过使用这些开环反应，取代2-或3-羟基，将咪唑基，碘，叠氮基和苄基巯基选择性地引入β-环糊精的次表面。官能化的环糊精具有修饰的糖苷亚基或修饰的拟铝基亚基，这使得疏水性腔与天然β-环糊精的疏水性腔略有不同。硫脲还与环糊精环氧化物反应。在这种情况下，会生成硫杂环丁烷和烯烃物种，而不是任何开环产物。通过改善反应条件，可以以中等至良好的产率制备环糊精烯烃，二烯和三烯衍生物。用氢化铝锂还原过[6-（叔丁基二甲基甲硅烷基）甲硅烷基]-β-环糊精高锰酸环氧化物产生过（3-脱氧）-β-环甘露聚糖。
• Synergetic effects in the enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by β-cyclodextrin–pillar[5]arene-hybridized hosts
  作者：Jiecheng Ji、Wanhua Wu、Xueqin Wei、Ming Rao、Dayang Zhou、Guo Cheng、Qiyong Gong、Kui Luo、Cheng Yang

  DOI：10.1039/d0cc02055a

  日期：——

  Photocyclodimerization of AC with β-CD–P5-hybridized hosts showed enantioselectivity critically relative to the absolute configuration of the central P5.

  AC与β-CD-P5杂化宿主的光环二聚化表现出对中心P5的绝对构型关键的对映选择性。
• Enhanced irregular photodimers and switched enantioselectivity by solvent and temperature in the photocyclodimerization of 2-anthracenecarboxylate with modified β-cyclodextrins
  作者：Xueqin Wei、Xingke Yu、Yuxue Zhang、Wenting Liang、Jiecheng Ji、Jiabin Yao、Ming Rao、Wanhua Wu、Cheng Yang

  DOI：10.1016/j.jphotochem.2018.11.038

  日期：2019.2

  (CDs) 7-11 were prepared for mediating the enantiodifferentiating [4 + 4] photocyclodimerization reactions of 2-anthracenecarboxylic acid (AC). The complexation behavior of these hosts with AC was studied by 1H NMR, UV–vis, circular dichroism spectroscopy and ITC titration. The product distribution and product’s ee turned out to be a critical function of the skeleton and periphery modifications of β-CD

  一系列初级face-或仲-表面-改性的β环糊精（CDS）的7 - 11被用于介导的enantiodifferentiating 2-蒽甲酸（AC）[4 + 4] photocyclodimerization反应制备。通过1 H NMR，UV-vis，圆二色谱和ITC滴定研究了这些宿主与AC的络合行为。产品分布和产品的ee证明是β-CD骨架和外围修饰的关键功能。在存在修饰的β-CDs的情况下，滑动的环二聚体5和6的总产率大大提高。与天然β-CD和其他β-CD衍生物相反，宿主9其中在β-CD的主面上引入苯基三唑基的化合物，提供对映体环二聚体6，对映体选择性高得多，为46％ee。深入研究了温度和盐添加剂的影响。有趣的是，在6 M CsCl的存在下，产品的手性随温度变化。在最佳条件下，宿主8以70％ee给出了滑环二聚体6，这是有报道的滑环二聚体的最高对映选择性。
• The Dependence of Catalytic Activities of Secondary Functional .BETA.-Cyclodextrins on Cavity Structures.
  作者：Wen-Hua CHEN、Satoko HAYASHI、Tsutomu TAHARA、Yasuyoshi NOGAMI、Toshitaka KOGA、Masatoshi YAMAGUCHI、Kahee FUJITA

  DOI：10.1248/cpb.47.588

  日期：——

  Secondary imidazole-appended β-cyclodextrin 5 with a nondistorted cavity synthesized from a novel intermediate 3-amino-3-deoxy-β-cyclodextrin exhibits much greater catalytic activity in the ester hydrolysis than its isomer 6 with a distorted cavity, indicating that the catalytic activities of secondary functional cyclodextrins are dependent on cavity structures.

  由新型中间体3-氨基-3-脱氧-β-环糊精合成的具有非扭曲空腔的仲咪唑β-环糊精5在酯水解中表现出比其具有扭曲空腔的异构体6更高的催化活性，表明催化活性二级功能环糊精的活性取决于空腔结构。
• Cyclodextrin-based class I aldolase enzyme mimics to catalyze crossed aldol condensations
  作者：De-Qi Yuan、Steven D. Dong、Ronald Breslow

  DOI：10.1016/s0040-4039(98)01717-1

  日期：1998.10

  A variety of mono- and unsymmetrical bifunctional P-cyclodextrins have been developed as efficient mimics of class I aldolases, some of which show a large rate acceleration and substrate selectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.