2^I-VI,3^I-VI,6^II,IV-VI-hexadeca-O-methyl-α-cyclomaltohexaose | 503590-80-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2^I-VI,3^I-VI,6^II,IV-VI-hexadeca-O-methyl-α-cyclomaltohexaose
• CAS: 503590-80-5
• 化学式: C₅₂H₉₂O₃₀
• 分子量: 1197.28
• InChiKey: MHNQIMIDIKPFTM-OQWQTNIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.59
• 重原子数：
  82.0
• 可旋转键数：
  22.0
• 环数：
  22.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  298.9
• 氢给体数：
  2.0
• 氢受体数：
  30.0

反应信息

• 作为反应物：
  描述：

  2^I-VI,3^I-VI,6^II,IV-VI-hexadeca-O-methyl-α-cyclomaltohexaose 在 吡啶 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 6¹,6³-Dideoxy-6¹,6³-diiodo-cG₆ permethylate
  参考文献：
  名称：

  Preparation of di-O-triphenylmethyl-(trityl)-cyclomalto-hexaoses and -cyclomaltoheptaoses and characterization of three positional isomers of each by the “hex-5-enose degradation”

  摘要：

  Regioisomeric 6l,6n-di-O-trityl-cyclomaltohexaoses (cG6s) or -cyclomaltoheptaoses (cG7s) were prepared by the reaction of cyclomaltohexaose (1, cG6) or cylomaltoheptaose (5, cG7) with chlorotriphenylmethane methane in pyridine and isolation by h.p.l.c. The regiochemical determination of each three ditrityl-substituted substituted derivatives has been accomplished by the "hex-5-enose degradation", followed by measurement of their f.a.b.-mass spectra.

  DOI：

  10.1016/0008-6215(92)80001-h
• 作为产物：
  描述：

  6¹,6³-Di-O-trtyl-cG₆ permethylate 在 溶剂黄146 作用下， 反应 1.0h， 生成 2^I-VI,3^I-VI,6^II,IV-VI-hexadeca-O-methyl-α-cyclomaltohexaose
  参考文献：
  名称：

  Preparation of di-O-triphenylmethyl-(trityl)-cyclomalto-hexaoses and -cyclomaltoheptaoses and characterization of three positional isomers of each by the “hex-5-enose degradation”

  摘要：

  Regioisomeric 6l,6n-di-O-trityl-cyclomaltohexaoses (cG6s) or -cyclomaltoheptaoses (cG7s) were prepared by the reaction of cyclomaltohexaose (1, cG6) or cylomaltoheptaose (5, cG7) with chlorotriphenylmethane methane in pyridine and isolation by h.p.l.c. The regiochemical determination of each three ditrityl-substituted substituted derivatives has been accomplished by the "hex-5-enose degradation", followed by measurement of their f.a.b.-mass spectra.

  DOI：

  10.1016/0008-6215(92)80001-h

文献信息

• Radical-Mediated C–H Functionalization: A Strategy for Access to Modified Cyclodextrins
  作者：Dimitri Alvarez-Dorta、Elisa I. León、Alan R. Kennedy、Angeles Martín、Inés Pérez-Martín、Ernesto Suárez

  DOI：10.1021/acs.joc.6b02241

  日期：2016.12.2

  A simple and efficient radical C–H functionalization to access modified cyclodextrins (CDs) has been developed. The well-defined conformation of glycosidic and aglyconic bonds in α-, β-, and γ-CDs favors the intramolecular 1,8-hydrogen atom transfer (HAT) promoted by the 6I-O-yl radical, which abstracts regioselectively the hydrogen at C5II of the contiguous pyranose. The C5II-radical evolves by a

  已开发出一种简单有效的自由基C–H功能化以获取修饰的环糊精（CD）。α-，β-和γ-CD中糖苷键和糖苷键的明确构象有利于6 I - O-自由基促进的分子内1,8-氢原子转移（HAT），该自由基选择性地提取氢在连续吡喃糖的C5 II处。该C5 II两个相邻的葡萄糖或可替代地之间-基团的演进通过极性交叉机构以稳定的1,3,5-三氧环触发一个的反转α- d葡萄糖成5- Ç -乙酰氧基-β-升-拥有1 C 4的同剂量单位构象。α-和β-CD的6 I，IV-和6 I，III-二醇的行为与一元醇相似，主要形成源自两个1,8-HAT连续过程的化合物。在6 I，II-二醇的情况下，相邻糖单元中的两个6- O-基团的接近允许通过1,8-HAT-β-分裂串联机制在CD骨架内形成独特的内酯环。在结晶的1，4-双（三氧杂环丁烷）-α-CD衍生物上进行的X射线衍射显示出主面朝着较窄的椭圆形严重变形。