2-β-D-glucopyranosylmercapto-benzoic acid methyl ester | 109472-90-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-β-D-glucopyranosylmercapto-benzoic acid methyl ester
• 英文别名: 2-β-D-Glucopyranosylmercapto-benzoesaeure-methylester
• CAS: 109472-90-4
• 化学式: C₁₄H₁₈O₇S
• 分子量: 330.359
• InChiKey: PEGXQWWBDNLOAR-CGUBKOMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.63
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  116.45
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-β-D-glucopyranosylmercapto-benzoic acid methyl ester 在 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 5'-(2-chlorophenyl)furan-2'-carbaldehyde-2-thio-β-D-glucopyranosyl benzoyl hydrazone
  参考文献：
  名称：

  Molecular Design and Synthesis of Novel Salicyl Glycoconjugates as Elicitors against Plant Diseases

  摘要：

  一种新的含有肼和肼酮基团的水杨酸糖缀合物系列被设计和合成。生物测定结果表明，这些新化合物在体外没有杀菌活性，但在体内对测试的真菌病原体显示出了显著的抗真菌活性。一些化合物在温室试验中的活性甚至优于商业杀真菌剂。RT-PCR分析结果显示，所设计的水杨酸糖缀合物能够诱导激素信号通路特异性标记基因LOX1和Cs-AOS2的表达，从而触发植物防御抵抗。

  DOI：

  10.1371/journal.pone.0108338
• 作为产物：
  描述：

  (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(methoxycarbonyl)phenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 2-β-D-glucopyranosylmercapto-benzoic acid methyl ester
  参考文献：
  名称：

  Synthesis and absolute structures of Mycoplasma pneumoniae β-glyceroglycolipid antigens

  摘要：

  just recently, a pair of beta-glycolipids was isolated from the cell membrane of Mycoplasma pneumoniae as a mixture of the two compounds. They are the major immunodeterminants of this pathogenic Mycoplasma and indicate high medicinal potential. They have a beta-(1 -> 6)-linked disaccharide structure close to each other: one has beta-D-galactopyranoside (beta-Gal-type 1) at the non-reducing terminal, and another has beta-D-glucopyranoside (beta-Glc-type 2). In the present Study, the first stereoselective synthesis was conducted for each of the two beta-glycolipids 1 and 2. H-1 NMR and TLC-immunostaining studies of the synthetic compounds enable LIS to establish the absolute structures having the beta-(1 -> 6)-linked disaccharides at the glycerol sn-3 position. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.09.028

文献信息

• Molecular design, synthesis and bioactivity of glycosyl hydrazine and hydrazone derivatives: Notable effects of the sugar moiety
  作者：Zining Cui、Xinling Yang、Yanxia Shi、Hirotaka Uzawa、Jingrong Cui、Hirofumi Dohi、Yoshihiro Nishida

  DOI：10.1016/j.bmcl.2011.09.068

  日期：2011.12

  hydrazone derivatives would improve after modification with sugars while keeping or modulating their notable biological activities, we designed and synthesized some glycosyl hydrazine and hydrazone derivatives. Bioassay results indicated that the antitumor activity of our previously prepared hydrazones reduced or disappeared after modification with sugars. On the contrary, some glycosyl derivatives displayed

  假设我们先前的derivatives衍生物在用糖修饰后会提高水溶性，同时保持或调节其显着的生物活性，我们设计并合成了一些糖基肼和衍生物。生物测定结果表明，用糖修饰后，我们先前制备的的抗肿瘤活性降低或消失。相反，一些糖基衍生物对选定的真菌表现出更好的抗真菌活性。显然，少量糖可以显着改变的生物活性。
• Über die Synthese von S-β-D-Glucopyranosiden verschiedener Derivate der 2-Mercaptobenzoesäure (Thiosalicylsäure) 6. Mitteilung „Über Phenolglykoside”
  作者：Günther Wagner

  DOI：10.1002/ardp.19572901005

  日期：——
• Evaluating the reactivity and stereoselectivity of salicyl-type thioglycosides as non-malodorous thioglycoside alternatives for oligosaccharide synthesis
  作者：Hirofumi Dohi、Risa Sakurai、Manami Tamura、Ryota Komai、Yoshihiro Nishida

  DOI：10.1080/07328303.2021.1921787

  日期：2021.3.31