2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl 2-methylprop-2-enoate | 130447-74-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl 2-methylprop-2-enoate
• CAS: 130447-74-4
• 化学式: C₁₂H₂₀O₈
• 分子量: 292.286
• InChiKey: KUQRLZZWFINMDP-GPTQDWHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 以20 mg的产率得到2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl 2-methylprop-2-enoate
  参考文献：
  名称：

  温和氢解条件下氢键辅助 1,2-顺式 O-糖基化

  摘要：

  利用 4,6-二苄氧基-1,3,5-三嗪-2-基 (DBT) β-糖基供体进行氢键辅助α-选择性糖基化反应，有效构建 1,2-顺式- α -天然产物中的糖苷键。该方法成功应用于具有简单保护化学的复杂寡糖衍生糖脂的直接合成。使用核磁共振光谱和 DFT 计算的机理研究为氢键辅助糖基化反应向α-特异性构建O-糖苷键提供了概念证明。

  DOI：

  10.1016/j.cclet.2022.107754

文献信息

• Interfacing Nanostructures to Biological Cells
  申请人：Chen Xing

  公开号：US20080199399A1

  公开（公告）日：2008-08-21

  Disclosed herein are methods and materials by which nanostructures such as carbon nanotubes, nanorods, etc. are bound to lectins and/or polysaccharides and prepared for administration to cells. Also disclosed are complexes comprising glycosylated nanostructures, which bind selectively to cells expressing glycosylated surface molecules recognized by the lectin. Exemplified is a complex comprising a carbon nanotube functionalized with a lipid-like alkane, linked to a polymer bearing repeated α-N-acetylgalactosamine sugar groups. This complex is shown to selectively adhere to the surface of living cells, without toxicity. In the exemplified embodiment, adherence is mediated by a multivalent lectin, which binds both to the cells and the α-N-acetylgalactosamine groups on the nanostructure.

  本文公开了一种将纳米结构（如碳纳米管、纳米棒等）与凝集素和/或多糖结合并准备用于细胞治疗的方法和材料。还公开了含有糖基化纳米结构的复合物，其可选择性地结合到表达被凝集素识别的糖基化表面分子的细胞上。本文举例说明了一种复合物，其包括一种碳纳米管，其被一个类脂样烷基功能化，并与一个带有重复α-N-乙酰半乳胺糖基团的聚合物连接。该复合物被证明可以选择性地附着在活细胞表面上，而不具有毒性。在所举例的实施例中，附着是通过多价凝集素介导的，该凝集素既结合细胞又结合纳米结构上的α-N-乙酰半乳胺基团。
• Enzymatic production of glycosylated synthons
  申请人：Institut National de la Recherche Agronomique (INRA)

  公开号：US10696995B2

  公开（公告）日：2020-06-30

  The present invention relates to a method for producing a glycosylated synthon or a monomer. Said method includes at least one step of placing at least one glycan-saccharase in the presence of at least one hydroxylated synthon and at least one saccharose. The invention also relates to a method for producing a glyco(co)polymer, including polymerizing at least two monomers separately obtained from the enzymatic glycosylation method according to the invention, and to a method for producing a glyco(co)polymer, preferably a block glyco(co)polymer, including coupling at least two monomers separately obtained from the enzymatic glycosylation method according to the invention.

  本发明涉及一种生产糖基化合物或单体的方法。该方法至少包括一个步骤，即在至少一种羟基化合素和至少一种糖存在的情况下，放置至少一种聚糖-糖酶。本发明还涉及一种生产糖（共）聚合物的方法，包括聚合至少两种分别从根据本发明的酶糖基化方法中获得的单体，以及一种生产糖（共）聚合物，最好是嵌段糖（共）聚合物的方法，包括偶联至少两种分别从根据本发明的酶糖基化方法中获得的单体。
• Glycosylation Using Unprotected Alkynyl Donors
  作者：Sreeman K. Mamidyala、M.G. Finn

  DOI：10.1021/jo901857x

  日期：2009.11.6

  Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in acetonitrile with 5% AuCl(3) for reaction with various primary alcohol acceptors, the latter used in 10-fold molar excess relative to donor. Donors containing the 2-butynyl group were more reactive, giving good yields of glycoside products at lower temperatures Secondary alcohols could also be used but with diminished efficiency. The propargylic family of donors is especially convenient because they can be easily prepared on large scale by Fischer glycosylation and stored indefinitely before chemoselective activation by the catalyst.
• WÄSSRIGE BESCHICHTUNGSZUSAMMENSETZUNG MIT NIEDRIGEM VOC-GEHALT
  申请人：BASF SE

  公开号：EP1957592A1

  公开（公告）日：2008-08-20
• PRODUCTION DE SYNTHONS GLYCOSYLES PAR VOIE ENZYMATIQUE
  申请人：Institut National de la Recherche Agronomique (INRA)

  公开号：EP3271469A1

  公开（公告）日：2018-01-24