allyl 2,3,4,6-tetra-O-allyl-α-D-glucopyranoside | 185564-68-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,4,6-tetra-O-allyl-α-D-glucopyranoside
• 英文别名: allyl-(tetra-O-allyl-α-D-glucopyranoside)；Allyl-(tetra-O-allyl-α-D-glucopyranosid)；(2S,3R,4S,5R,6R)-2,3,4,5-tetrakis(prop-2-enoxy)-6-(prop-2-enoxymethyl)oxane
• CAS: 185564-68-5
• 化学式: C₂₁H₃₂O₆
• 分子量: 380.481
• InChiKey: UCHNNEUPIPRPNU-ADAARDCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 2,3,4,6-tetra-O-allyl-α-D-glucopyranoside 在 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 2-[3-[[(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[3-(2-aminoethylsulfanyl)propoxy]oxan-2-yl]methoxy]propylsulfanyl]ethanamine
  参考文献：
  名称：

  A New Type of Carbohydrate Clustering: Synthesis of a Pentavalent Glycocluster Based on a Carbohydrate Core

  摘要：

  将半胱胺盐酸盐光加到过烯丙基化的 D-葡萄糖上可产生一种糖源五胺，这种五胺可作为碳水化合物的核心分子，用于形成糖团和糖二聚体，并在与过乙酰化的甘露基异硫氰酸酯反应后产生一种五硫脲桥接的糖团。

  DOI：

  10.1055/s-2008-1067191
• 作为产物：
  描述：

  葡萄糖 在 盐酸 、 sodium hydroxide 作用下， 生成 allyl 2,3,4,6-tetra-O-allyl-α-D-glucopyranoside
  参考文献：
  名称：

  Allyl Ethers of Carbohydrates. III. Ethers of Glucose and Galactose^1a

  摘要：

  DOI：

  10.1021/ja01227a050

文献信息

• Oligomannoside mimetics by glycosylation of ‘octopus glycosides’ and their investigation as inhibitors of type 1 fimbriae-mediated adhesion of Escherichia coli
  作者：Michael Dubber、Oliver Sperling、Thisbe K. Lindhorst

  DOI：10.1039/b610741a

  日期：——

  carry highly complex oligosaccharide portions. To elucidate the biological role and function of the glycocalyx in cell-cell communication and cellular adhesion processes, glycomimetics have become targets of glycosciences, which resemble the composition and structural complexity of the glycocalyx constituents. Here, we report about the synthesis of a class of oligosaccharide mimetics of a high-mannose

  真核细胞的糖萼由糖缀合物组成，其携带高度复杂的寡糖部分。为了阐明糖萼在细胞-细胞通讯和细胞粘附过程中的生物学作用和功能，糖模拟物已成为糖科学的目标，类似于糖萼成分的组成和结构复杂性。在这里，我们报告有关高甘露糖类型的一类寡糖模拟物的合成，该模拟物是通过对间隔的单糖和寡糖核心进行甘露糖基化作用而获得的。这些以碳水化合物为中心的簇甘露糖苷已被靶向作为甘露糖特异性细菌粘附的抑制剂，这种粘附是由所谓的1型菌毛介导的。通过ELISA测定了它们的抑制能力，并将其与甲基甘露糖苷以及一系列甘露糖苷进行了比较，最后是多糖甘露聚糖。获得的结果提示根据大分子而非多价效应对细菌粘附机制的新解释。
• Synthesis of octopus glycosides: core molecules for the construction of glycoclusters and carbohydrate-centered dendrimers
  作者：Michael Dubber、Thisbe K. Lindhorst

  DOI：10.1016/s0008-6215(98)00155-4

  日期：1998.8

  spacer glycosides of an “octopus” type, taking advantage of the rich chemistry of the allyl ether function. Thus, carbohydrate-derived pentaaldehydes, pentaalcohols and pentaamines with different spacer lengths were obtained by ozonolysis, reductive amination, hydroboration or photoaddition of cysteamine hydrochloride, respectively. The new octopus glycosides are useful core molecules for the synthesis of

  摘要将烯丙基α-d-吡喃葡萄糖苷高丽烷基化为烯丙基2,3,4,6-四-O-烯丙基-α-d-吡喃葡萄糖苷，然后将其转变成一系列均匀功能化的“章鱼”型间隔苷烯丙基醚功能丰富的化学物质的优势。因此，分别通过臭氧分解，半胱胺盐酸盐的臭氧分解，还原胺化，硼氢化或光加成，获得了具有不同间隔长度的碳水化合物衍生的五醛，五醇和五胺。新的章鱼糖苷是有用的核心分子，用于糖簇的合成和以碳水化合物为中心的树状聚合物的构建。
• Synthesis of chiral carbohydrate-centered dendrimers
  作者：Michael Dubber、Thisbe K. Lindhorst

  DOI：10.1039/a800560e

  日期：——

  D-Glucose was converted into its per-O-(2-aminoethyl)-functionalized derivative 4, which served as initiator core for the construction of the chiral, monodisperse PAMAM-type carbohydrate-centered hybrid dendrimer 7.

  D-Glucose 被转化为过-O-（2-氨基乙基）官能化衍生物 4，作为构建手性、单分散 PAMAM 型以碳水化合物为中心的混合树枝状聚合物 7 的引发剂核心。
• Synthesis, CI-MS Analyses and Preliminary Biological Evaluation of a Novel Library of Hydrophobic Persulfide-Spacers α-Alkyl Glycosides
  作者：Hammed H. Hassan

  DOI：10.2174/157017810790796372

  日期：2010.3.1

  We report the synthesis of novel polyether-based polyols derived from simple glycosides that bear sulfur spacers in the attempt to potentially provide new antibiotics. The CI-MS demonstrated the stepwise and successive fission of the sulfide-spacer groups; however, it does not distinguish between the alditols having different arrangement of O(CH2)(3)-S(CH2)(2)OH groups. The investigated compounds exhibited antimicrobial activities against Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli and antifungal activities against Candida albicans at a concentration of 1 mg / ml in DMF.
• Octopus glycosides: multivalent molecular platforms for testing carbohydrate recognition and bacterial adhesion
  作者：Thisbe K. Lindhorst、Michael Dubber

  DOI：10.1016/j.carres.2014.06.032

  日期：2015.2

  Multivalency of carbohydrate-protein interactions is critical for cell adhesion, including attachment of bacteria to their host cells. To investigate specific parameters of multivalency effects, a variety of multivalent glycoconjugates has been designed according to different mimetic approaches. Some 15 years ago, carbohydrates were elaborated as multivalent scaffold molecules for the preparation of carbohydrate-centred 'octopus glycosides' as well as of other carbohydrate-centred glycoconjugates. The beginning of this research is reported from a historical perspective and a selection of interesting applications is highlighted. (C) 2014 Elsevier Ltd. All rights reserved.