6^A-(N-dansyl-L-cysteine)-6^B-tosyl-γ-cyclodextrin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6^A-(N-dansyl-L-cysteine)-6^B-tosyl-γ-cyclodextrin
• 英文别名: (2R)-2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-3-[[(1S,3R,5R,6S,8R,10R,11S,13S,15S,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36S,38R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R,50R,51R,52R,53R,54R,55R,56R)-41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56-hexadecahydroxy-5,10,25,30,35,40-hexakis(hydroxymethyl)-20-[(4-methylphenyl)sulfonyloxymethyl]-2,4,7,9,12,14,17,19,22,24,27,29,32,34,37,39-hexadecaoxanonacyclo[36.2.2.23,6.28,11.213,16.218,21.223,26.228,31.233,36]hexapentacontan-15-yl]methylsulfanyl]propanoic acid
• 化学式: C₇₀H₁₀₂N₂O₄₅S₃
• 分子量: 1787.76
• InChiKey: OIKNPJHKNSAXEH-SFQHSRHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -12.1
• 重原子数：
  120
• 可旋转键数：
  19
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  765
• 氢给体数：
  24
• 氢受体数：
  48

反应信息

• 作为反应物：
  描述：

  6^A-(N-dansyl-L-cysteine)-6^B-tosyl-γ-cyclodextrin 在 N,N-二甲基甲酰胺 作用下， 以55%的产率得到
  参考文献：
  名称：

  Clockwise–counterclockwise differentiation on the upper rim of a monofunctional γ-cyclodextrin: efficient topological control in the syntheses of capped cyclodextrins

  摘要：

  6A-(N-丹辛基-L-半胱氨酸)-γ-环糊精的分子内缩合仅在众多羟基中的6B-OH处发生，形成具有外拓扑的相应内酯。

  DOI：

  10.1039/b612437b
• 作为产物：
  描述：

  丹酰氯 、 L-半胱氨酸盐酸盐无水物 、 6^A,6^B-Di-O-(p-tosyl)-γ-cyclodextrin 在 sodium carbonate 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.5h， 以36%的产率得到6^A-(N-dansyl-L-cysteine)-6^H-tosyl-γ-cyclodextrin
  参考文献：
  名称：

  Hetero-bifunctional γ-cyclodextrins having dansylcysteine and tosyl groups at two adjacent sugar units: synthesis and determination of regio-chemistry

  摘要：

  Ditosylation of two adjacent 6-positions of gamma-cyclodextrin, subsequent mono-substitution with L-cysteine and final condensation with dansyl chloride afford the title compounds whose clockwise and counterclockwise isomers are separated from each other and their regio-chemistry is unambiguously determined by a new strategy based on the combination of enzyme degradation of the hetero-bifunctional gamma-cyclodextrin to the corresponding disubstituted maltotriose and fragmentation analysis of the latter by PSD-MS technique. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.003

文献信息

• Hetero-bifunctional γ-cyclodextrins having dansylcysteine and tosyl groups at two adjacent sugar units: synthesis and determination of regio-chemistry
  作者：Hua Yu、Yuji Makino、Makoto Fukudome、Ru-Gang Xie、De-Qi Yuan、Kahee Fujita

  DOI：10.1016/j.tetlet.2007.03.003

  日期：2007.4

  Ditosylation of two adjacent 6-positions of gamma-cyclodextrin, subsequent mono-substitution with L-cysteine and final condensation with dansyl chloride afford the title compounds whose clockwise and counterclockwise isomers are separated from each other and their regio-chemistry is unambiguously determined by a new strategy based on the combination of enzyme degradation of the hetero-bifunctional gamma-cyclodextrin to the corresponding disubstituted maltotriose and fragmentation analysis of the latter by PSD-MS technique. (c) 2007 Elsevier Ltd. All rights reserved.
• Clockwise–counterclockwise differentiation on the upper rim of a monofunctional γ-cyclodextrin: efficient topological control in the syntheses of capped cyclodextrins
  作者：Hua Yu、De-Qi Yuan、Yuji Makino、Makoto Fukudome、Ru-Gang Xie、Kahee Fujita

  DOI：10.1039/b612437b

  日期：——

  Intramolecular condensation of 6A-(N-dansyl-L-cysteine)-γ-cyclodextrin occurred only at 6B-OH of the many OH groups to afford the corresponding lactone with an exo-topology.

  6A-(N-丹辛基-L-半胱氨酸)-γ-环糊精的分子内缩合仅在众多羟基中的6B-OH处发生，形成具有外拓扑的相应内酯。