1-C-allyl-1-deoxy-3,4-O-isopropylidene-6-O-dimethyltertbutylsilyl-α-D-galactopyranoside | 1010796-88-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-C-allyl-1-deoxy-3,4-O-isopropylidene-6-O-dimethyltertbutylsilyl-α-D-galactopyranoside
• 英文别名: 3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-1-allyl-α-D-galactopyranoside
• CAS: 1010796-88-9
• 化学式: C₁₈H₃₄O₅Si
• 分子量: 358.55
• InChiKey: RCEIUQINOIWNPO-RBGFHDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-C-allyl-1-deoxy-3,4-O-isopropylidene-6-O-dimethyltertbutylsilyl-α-D-galactopyranoside 在 copper(ll) sulfate pentahydrate 、 四丁基氟化铵 、 sodium hydride 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 mineral oil 为溶剂， 反应 45.17h， 生成
  参考文献：
  名称：

  单糖的结构单元，用于合成包括大环在内的支架。烯丙基叠氮化物重排，叠氮-炔烃环加成和闭环复分解的应用

  摘要：

  需要合成具有天然产物特征的化合物以增加用于筛选的化合物的多样性和生物学相关性。这些包括具有多个立体生成中心和各种功能组的新框架/支架。碳水化合物是可再生的，容易获得的并且具有立体化学多样性和功能性。在本文中，使用衍生自具有烯，炔和有机叠氮化物官能团的单糖的结构单元。利用RuAAC，CuAAC和热促进的叠氮化物-炔烃环加成反应，烯丙基叠氮化物（Winstein）重排和闭环易位，采用多样性导向合成的构建对配对策略，从而形成多羟基化的小，中和大环含环骨架。有可能植入附件（例如

  DOI：

  10.1016/j.tet.2020.131495
• 作为产物：
  描述：

  1-C-allyl-1-deoxy-3,4-O-isopropylidene-α-D-galactopyranoside 、 叔丁基二甲基氯硅烷 在 4-二甲氨基吡啶 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 以100%的产率得到1-C-allyl-1-deoxy-3,4-O-isopropylidene-6-O-dimethyltertbutylsilyl-α-D-galactopyranoside
  参考文献：
  名称：

  The Importance of Hydration for Inhibiting Ice Recrystallization with C-Linked Antifreeze Glycoproteins

  摘要：

  The role of hydration in modulating solution conformation, molecular recognition, and biological activity of oligosaccharides, proteins, and nucleotides is widely recognized but is often neglected when investigating many biological processes such as the mechanism by which biological antifreezes inhibit the growth of ice. We have investigated the relationship between carbohydrate configuration and recrystallization-inhibition (RI) activity in functional C-linked antifreeze glycoprotein (AFGP) analogues using a series of analogues 1-4. While analogues 1-4 did not show any thermal hysteresis (TH) activity, 1 did exhibit weak dynamic ice shaping indicating that this compound had the ability to interact with the ice lattice. The D-mannose and D-talose analogues (3 and 4, respectively) exhibited very weak RI activity with mean largest grain size values similar to phosphate buffered saline, the negative control. D-Glucose analogue 2 exhibited moderate RI activity while D-galactose analogue 1 was the most potent analogue with RI activity comparable to the native AFGP 8. These results suggest that the configuration of the carbohydrate moiety in C-linked AFGP analogues is extremely important and modulates recrystallization-inhibition activity. It seems likely that differences in hydration for each C-linked pyranose alter the compatibility of the carbohydrate moiety with the three-dimensional hydrogen-bonded network of supercooled bulk water. Consequently, the energy associated with transferring a water molecule to the ice lattice changes and can result in inhibition of ice growth. These results emphasize the importance of continued studies to further elucidate the role of hydration in antifreeze activity.

  DOI：

  10.1021/ja7103262

文献信息

• Decorated Macrocycles via Ring-Closing Double-Reductive Amination. Identification of an Apoptosis Inducer of Leukemic Cells That at Least Partially Antagonizes a 5-HT2 Receptor
  作者：Jian Zhou、Mairead Reidy、Ciaran O’Reilly、Dilip V. Jarikote、Arvind Negi、Afshin Samali、Eva Szegezdi、Paul V. Murphy

  DOI：10.1021/acs.orglett.5b00404

  日期：2015.4.3

  A build-couple-pair strategy, including double-reductive amination macrocyclization, has been used to generate decorated macrocycles (eannaphanes) with an embedded triazole and monosaccharide. Biological screening led to the identification of an inducer of apoptosis in leukemic cells, which acts at least partially as a 5-HT2 antagonist.
• Hydration IndexA Better Parameter for Explaining Small Molecule Hydration in Inhibition of Ice Recrystallization
  作者：Roger Y. Tam、Sandra S. Ferreira、Pawel Czechura、Jennifer L. Chaytor、Robert N. Ben

  DOI：10.1021/ja806284x

  日期：2008.12.24

  Several simple mono- and disaccharides have been assessed for their ability to inhibit ice recrystallization. Two carbohydrates were found to be effective recrystallization inhibitors. D-Galactose (1) was the best monosaccharide and D-melibiose (5) was the most active disaccharide. The ability of each carbohydrate to inhibit ice growth was correlated to its respective hydration number reported in the literature. A hydration number reflects the number of tightly bound water molecules to the carbohydrate and is a function of carbohydrate stereochemistry. It was discovered that using the absolute hydration number of a carbohydrate does not allow one to accurately predict its ability to inhibit ice recrystallization. Consequently, we have defined a hydration index in which the hydration number is divided by the molar volume of the carbohydrate. This new parameter not only takes into account the number of water molecules tightly bound to a carbohydrate but also the size or volume of a particular solute and ultimately the concentration of hydrated water molecules. The hydration index of both mono- and disaccharides correlates well with experimentally measured RI activity. C-Linked derivatives of the monosaccharides appear to have RI activity comparable to that of their O-linked saccharides but a more thorough investigation is required. The relationship between carbohydrate concentration and RI activity was shown to be noncolligative and a 0.022 M solution of D-galactose (1) and C-linked galactose derivative (10) inhibited recrystallization as well as a 3% DMSO solution. The carbohydrates examined in this study did not possess any thermal hysteresis activity (selective depression of freezing point relative to melting point) or dynamic ice shaping. As such, we propose that they are inhibiting recrystallization at the interface between bulk water and the quasi liquid layer (a semiordered interface between ice and bulk water) by disrupting the preordering of water.