6^A-O-(diphenoxyphosphoryl)-β-cyclodextrin | 62802-60-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6^A-O-(diphenoxyphosphoryl)-β-cyclodextrin
• 英文别名: mono[6-O-(diphenoxyphosphoryl)]-β-cyclodextrin；mono-(6-O-diphenoxyphosphoryl)-β-cyclodextrin；diphenyl [(1S,3R,5R,6S,8R,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)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-5,15,20,25,30,35-hexakis(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]nonatetracontan-10-yl]methyl phosphate
• CAS: 62802-60-2
• 化学式: C₅₄H₇₉O₃₈P
• 分子量: 1367.17
• InChiKey: WVWPSDLHQGHJJO-RJULKEFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11.4
• 重原子数：
  93
• 可旋转键数：
  13
• 环数：
  23.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  579
• 氢给体数：
  20
• 氢受体数：
  38

反应信息

• 作为反应物：
  描述：

  6^A-O-(diphenoxyphosphoryl)-β-cyclodextrin 在 platinum(IV) oxide 水 、 氢气 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以146 mg的产率得到6^A-O-phosphono-β-cyclodextrin
  参考文献：
  名称：

  Effective synthesis of negatively charged cyclodextrins. Selective access to phosphate cyclodextrins

  摘要：

  We report the selective preparation of alpha- and beta-cyclodextrins bearing one and two phosphate moieties on the primary rim. These compounds were prepared by selective O-debenzylation of fully protected derivatives, followed by phosphorylation and deprotection. The synthesis of an a-cyclodextrin with both, a carboxylic group and a phosphate moiety on primary positions is also described. Title compounds are examples of negatively charged cyclodextrins that might be of interest in studying the complexation of cationic guests. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.094
• 作为产物：
  描述：

  6^A-O-(diphenoxyphosphoryl)-eicosa-O-benzyl-β-cyclodextrin 在 palladium dihydroxide 氢气 、 三氟乙酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 48.0h， 生成 6^A-O-(diphenoxyphosphoryl)-β-cyclodextrin
  参考文献：
  名称：

  Effective synthesis of negatively charged cyclodextrins. Selective access to phosphate cyclodextrins

  摘要：

  We report the selective preparation of alpha- and beta-cyclodextrins bearing one and two phosphate moieties on the primary rim. These compounds were prepared by selective O-debenzylation of fully protected derivatives, followed by phosphorylation and deprotection. The synthesis of an a-cyclodextrin with both, a carboxylic group and a phosphate moiety on primary positions is also described. Title compounds are examples of negatively charged cyclodextrins that might be of interest in studying the complexation of cationic guests. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.094

文献信息

• A Convenient Procedure for the Synthesis of 6-<i>O</i>-Mono-Phosphate β-Cyclodextrins
  作者：Siphamandla Simelane、Brillance Bhekie Mamba、Xavier Yangkou Mbianda

  DOI：10.1080/10426507.2013.797419

  日期：2013.12.1

  The synthesis of -cyclodextrin derivatives bearing one phosphate group on the primary rim is reported. These compounds were prepared in good to excellent yields, by reacting -cyclodextrin with dialkyl chlorophosphates in the presence of 4-dimethyl amino pyridine (DMAP) catalyst and dimethylformamide (DMF) as solvent. The methodology described is highly selective and the purification of the title compounds is simple, because difficulties due to phosphate regioisomers mixture are avoided.
• Molecular Recognition Study on Supramolecular System. 14.¹ Synthesis of Modified Cyclodextrins and Their Inclusion Complexation Thermodynamics with <scp>l</scp>-Tryptophan and Some Naphthalene Derivatives
  作者：Yu Liu、Bao-Hang Han、Bin Li、Yi-Min Zhang、Peng Zhao、Yun-Ti Chen、Takehiko Wada、Yoshihisa Inoue

  DOI：10.1021/jo971466b

  日期：1998.3.1

  A series of beta-cyclodextrin derivatives, carrying pyridinio (4-6), phosphonyl (7, 8), seleno (9-11), m-and p-picolinyl (12, 13), o-chloroanilino (16), 8-quinolyl. (17), furfuryl (18), and 9-fluorenyl (19) moieties in the side chain, were newly synthesized, and their complexation behavior was assessed and discussed thermodynamically, using L-tryptophan and a few naphthalene derivatives as representative guests. Calorimetric titrations have been performed at 25.0 degrees C in buffered aqueous solution (pH 7.20) to give the complex stability constants and thermodynamic parameters for the 1:1 inclusion complexation of these guests with the native and modified alpha-, beta-, and/or gamma-cyclodextrins (1-20). All of the chemical modifications to the primary side of cyclodextrins examined led to significant changes in complex stability and thermodynamic parameters, which are elucidated in terms of the conformational, electrostatic, hydrogen-bonding, and hydration effects. Thermodynamically, the inclusion complexation is mainly enthalpy-driven with a negative or minor positive entropic contribution, which in some cases determines the complex stability. The induced circular dichroism spectral analyses of these cyclodextrin derivatives indicated that the aromatic moiety in modified beta-cyclodextrins (4-6, 9-19) only shallowly penetrates into the hydrophobic cavity of beta-cyclodextrin, while the phenyl phosphate and fluorenyl moieties in 7 and 20 are embedded into the hydrophobic cavity of beta-cyclodextrin because of the longer linking chain. Using all the thermodynamic data for a wide variety of cyclodextrin derivatives obtained in this and previous studies, the entropy changes (T Delta S) were plotted against the enthalpy changes (Delta H) to give an excellent linear relationship. The slope (alpha) of 1.02 and an intercept (T Delta S-o) of 4.3 of the regression line indicate substantial conformational changes and extensive desolvation caused upon complexation,respectively.
• Liu, Yu; Li, Bin; Han, Bao-Hang, Journal of the Chemical Society. Perkin transactions II, 1997, # 7, p. 1275 - 1278
  作者：Liu, Yu、Li, Bin、Han, Bao-Hang、Li, Yu-Mei、Chen, Rong-Ti

  DOI：——

  日期：——
• Effective synthesis of negatively charged cyclodextrins. Selective access to phosphate cyclodextrins
  作者：Óscar López、Mikael Bols

  DOI：10.1016/j.tet.2008.05.094

  日期：2008.8

  We report the selective preparation of alpha- and beta-cyclodextrins bearing one and two phosphate moieties on the primary rim. These compounds were prepared by selective O-debenzylation of fully protected derivatives, followed by phosphorylation and deprotection. The synthesis of an a-cyclodextrin with both, a carboxylic group and a phosphate moiety on primary positions is also described. Title compounds are examples of negatively charged cyclodextrins that might be of interest in studying the complexation of cationic guests. (C) 2008 Elsevier Ltd. All rights reserved.