6^A,6^B-Di-O-(p-tosyl)-γ-cyclodextrin | 104901-62-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6^A,6^B-Di-O-(p-tosyl)-γ-cyclodextrin
• 英文别名: 6A,6B-bis-tosyl-γ-cyclodextrin；[(1S,3R,5R,6S,8R,10R,11S,13R,15R,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)-15-[(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-20-yl]methyl 4-methylbenzenesulfonate
• CAS: 104901-62-4
• 化学式: C₆₂H₉₂O₄₄S₂
• 分子量: 1605.52
• InChiKey: FNKBHNQCWBRSAD-FWDQMINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13.1
• 重原子数：
  108
• 可旋转键数：
  14
• 环数：
  32.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  696
• 氢给体数：
  22
• 氢受体数：
  44

反应信息

• 作为反应物：
  描述：

  6^A,6^B-Di-O-(p-tosyl)-γ-cyclodextrin 在 水 、 sodium chloride 、 calcium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 96.0h， 以71.3%的产率得到[(2R,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-[(4-methylphenyl)sulfonyloxymethyl]oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Fujita, Kahee; Tahara, Tsutomu; Koga, Toshitaka, Chemistry Letters, 1990, # 5, p. 743 - 746

  摘要：

  DOI：
• 作为产物：
  描述：

  γ-环糊精 生成 6^A,6^B-Di-O-(p-tosyl)-γ-cyclodextrin
  参考文献：
  名称：

  FUJITA, KAHEE;YAMAMURA, HATSUO;IMOTO, TAIJI;FUJIOKA, TOSHIRO;MIHASHI, KUN+, J. ORG. CHEM., 53,(1988) N 9, 1943-1947

  摘要：

  DOI：

文献信息

• Ammonia-Driven Chirality Inversion and Enhancement in Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate Mediated by Diguanidino-γ-cyclodextrin
  作者：Jiabin Yao、Zhiqiang Yan、Jiecheng Ji、Wanhua Wu、Cheng Yang、Masaki Nishijima、Gaku Fukuhara、Tadashi Mori、Yoshihisa Inoue

  DOI：10.1021/ja5032908

  日期：2014.5.14

  In the supramolecular photocyclodimerization of 2-anthracenecarboxylate mediated by 6(A),6(D)-diguanidino-γ-cyclodextrin (CD), the chiral sense and enantiomeric excess of the photoproduct were dynamic functions of temperature and cosolvent to afford the (M)-anti head-to-head cyclodimer in 64% ee in aqueous methanol at -70 °C but the antipodal (P)-isomer in 86% ee in aqueous ammonia at -85 °C, while

  在 6(A),6(D)-二胍基-γ-环糊精 (CD) 介导的 2-蒽羧酸超分子光环二聚反应中，光产物的手性和对映体过量是温度和助溶剂的动态函数，以提供 (M )-抗头对头环二聚体在 64% ee 的甲醇水溶液中在 -70 °C 但对映 (P)-异构体在 86% ee 的氨水中在 -85 °C，而相应的二氨基-γ-CD宿主没有表现出这种不寻常的光致变色行为。ee 景观对温度非常陡峭，并且对氨含量进行符号反转，以揭示在低氨含量和高氨含量下相反的温度依赖性，对此，溶剂结构和/或胍-羧酸盐相互作用模式的改变将是负责任的。
• Template-Assisted Stereoselective Photocyclodimerization of 2-Anthracenecarboxylic Acid by Bispyridinio-Appended γ-Cyclodextrin
  作者：Hiroshi Ikeda、Takashi Nihei、Akihiko Ueno

  DOI：10.1021/jo0482817

  日期：2005.2.1

  controlling the stereoselectivity of photocyclodimerization of 2-anthracenecarboxylate. When the photocyclodimerization of 2-anthracenecarboxylate was carried out in the presence of A,E-bispyridinio-appended γ-CD, the relative yield of one of the configurational isomers, the head-to-head/anti-isomer, was increased 1.8-fold compared to the corresponding yield in the presence of unmodified γ-CD or in the absence

  制备了4种双吡啶并加成的γ-环糊精（γ-CD），以制备用于控制2-蒽羧酸酯的光环二聚立体选择性的分子瓶。当在A，E-双吡啶并附有γ-CD的存在下进行2-蒽羧酸酯的光环二聚化时，其中一种构型异构体（头对头/反异构体）的相对产率提高了1.8-在未修饰的γ-CD存在下或在不存在任何γ-CD的情况下，其收率是相应收率的三倍。与未修饰的γ-CD相比，通过添加双吡啶并附加的γ-CD，光环二聚反应产物的光学收率也提高了10倍以上。
• Supramolecular Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate Mediated by Capped γ-Cyclodextrins: Critical Control of Enantioselectivity by Cap Rigidity
  作者：Cheng Yang、Tadashi Mori、Yoshihisa Inoue

  DOI：10.1021/jo800533y

  日期：2008.8.1

  with a rigid biphenyl cap gave the antipodal 2 in −58% ee. Interestingly, the ee of 2 mediated by flexibly capped γ-CDs was highly sensitive to the temperature variation as a consequence of large differential entropy changes in the enantiodifferentiation process. In contrast, the entropy effect does not appear to play a significant role in the photocyclodimerization of AC with rigidly capped γ-CDs.

  合成了一系列经封端和非封端的芳香族基团修饰的γ-环糊精（CD），以介导2-蒽羧酸（AC）的对映增差性[4 + 4]光环二聚。通过圆二色性，UV-vis和NMR光谱研究了这些γ-CD与AC的络合行为，揭示了在所有情况下稳定的1：2主-客体络合物的形成。结果显示，在带有加盖和未加盖的γ-CD中，带有联结A和D葡萄糖单元的联苯基的加盖的γ-CD最严格地限制了所包含的AC分子。通过封端的γ-CD的介导的AC的Photocyclodimerization显着改善了的产率和对映体过量（ee）头-头photodimer 3。ee和的绝对配置syn-to-to-tail光电二聚体2严格取决于封盖的刚性。因此，柔性加帽和边缘取代的γ-CD在中等ee处提供2约为40％，而带有刚性联苯帽的γ-CD在对映体2中提供-58％ee。有趣的是2的ee由于对映分化过程中存在较大的熵差变化，因此由柔性帽盖的γ-CD介导的γ
• 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.
• FUJITA, KAHEE;TAHARA, TSUTOMU;KOGA, TOSHITAKA, CHEM. LETT.,(1990) N, C. 743-746
  作者：FUJITA, KAHEE、TAHARA, TSUTOMU、KOGA, TOSHITAKA

  DOI：——

  日期：——