galactosyl amine | 70145-20-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: galactosyl amine
• 英文别名: [(2R,3S,4S,5R)-3,4,5-triacetyloxy-6-aminooxan-2-yl]methyl acetate
• CAS: 70145-20-9
• 化学式: C₁₄H₂₁NO₉
• 分子量: 347.322
• InChiKey: LMVYBLMOENOGGK-RRYROLNDSA-N

物化性质

• 沸点：
  411.6±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  galactosyl amine 在 molecular sieve 、 sodium sulfate 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 20.0h， 生成 1-((2R,3R,4S,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Tietze, Lutz F.; Bergmann, Andreas, Angewandte Chemie, 1985, vol. 97, # 2, p. 135 - 136

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,4,6-D-葡萄糖五乙酸酯 在 palladium 10% on activated carbon 、 氢溴酸 、 氢气 、 乙酸酐 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 26.5h， 生成 galactosyl amine
  参考文献：
  名称：

  Synthesis and immunostimulatory activity of sugar-conjugated TLR7 ligands

  摘要：

  Toll-like receptors (TLRs) are a type of pattern recognition receptors (PRRs), which are activated by recognizing pathogen-associated molecular patterns (PAMPs). The activation of TLRs initiates innate immune responses and subsequently leads to adaptive immune responses. TLR agonists are effective immuomodulators in vaccine adjuvants for infectious diseases and cancer immunotherapy. In exploring hydrophilic small molecules of TLR7 ligands using the cell-targeted property of a vaccine adjuvant, we conjugated 1V209, a small TLR7 ligand molecule, with various low or middle molecular weight sugar molecules that work as carriers. The sugar-conjugated 1V209 derivatives showed increased water solubility and higher immunostimulatory activity in both mouse and human cells compared to unmodified 1V209. The improved immunostimulatory potency of sugar-conjugates was attenuated by an inhibitor of endocytic process, cytochalasin D, suggesting that conjugation of sugar moieties may enhance the uptake of TLR7 ligand into the endosomal compartment. Collectively our results support that sugar-conjugated TLR7 ligands are applicable to novel drugs for cancer and vaccine therapy.

  DOI：

  10.1016/j.bmcl.2019.126840

文献信息

• A new efficient approach to N-linked glycopeptoids
  作者：Klaus Burger、Christoph Böttcher、Gabor Radics、Lothar Hennig

  DOI：10.1016/s0040-4039(01)00351-3

  日期：2001.4

  A preparatively simple synthesis of N-linked glycopeptoids from glycosylamine and imino diacetic acid using hexafluoroacetone as protecting and activating agent is described.

  描述了使用六氟丙酮作为保护和活化剂由糖胺和亚氨基二乙酸制备N-连接的糖肽的简单制备方法。
• Synthesis of Glycosylamines from Glycosyl Isothiocyanates and Bis(tributyltin) Oxide
  作者：Joaquin Isac-García、Francisco G. Calvo-Flores、Fernando Hernández-Mateo、Francisco Santoyo-González

  DOI：10.1002/1099-0690(200101)2001:2<383::aid-ejoc383>3.0.co;2-n

  日期：2001.1

  The synthesis of glycopyranosylamines is described from the reaction of glycopyranosyl isothiocynates with bis(tributyltin) oxide. The method is simple and efficient allowing, under very mild conditions, the synthesis of N-acyl glycopyranosylamines in one pot. The reactions were performed using both 2-deoxy-2-iodo glycopyranosyl isothiocyanates and glycopyranosyl isothiocyanates derived from mono-

  吡喃糖基胺的合成是通过吡喃糖基异硫氰酸酯与双（三丁基锡）氧化物的反应来描述的。该方法简单有效，允许在非常温和的条件下在一锅中合成 N-酰基吡喃糖胺。使用衍生自单糖和二糖的 2-脱氧-2-碘吡喃糖基异硫氰酸酯和吡喃糖基异硫氰酸酯进行反应。当起始材料是 α-吡喃葡萄糖基衍生物时观察到异构化。该方法也已用于制备几种糖基氨基酸。
• [EN] COMPOUNDS TARGETING THE CELL INVASION PROTEIN COMPLEX, THEIR PHARMACEUTICAL COMPOSITIONS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS CIBLANT LE COMPLEXE PROTÉIQUE D'INVASION CELLULAIRE, LEURS COMPOSITIONS PHARMACEUTIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ROYAL INST FOR THE ADVANCEMENT OF LEARNING MCGILL UNIVERSITY

  公开号：WO2013059927A1

  公开（公告）日：2013-05-02

  The present application relates to the compounds of formula I (I) as well as their use for inhibiting at least one of AKT-1, FAK and PKCα and in the treatment and/or prevention of metastatic diseases.

  本申请涉及到I式化合物（I）以及它们在抑制AKT-1、FAK和PKCα中至少一种方面的使用，以及在治疗和/或预防转移性疾病方面的使用。