methyl 2,3,4-tri-O-acetyl-6-O-p-toluenesulfonyl-β-D-galactopyranoside | 112716-28-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-6-O-p-toluenesulfonyl-β-D-galactopyranoside
• 英文别名: methyl-[O²,O³,O⁴-triacetyl-O⁶-(toluene-4-sulfonyl)-β-D-galactopyranoside]；Methyl-[O²,O³,O⁴-triacetyl-O⁶-(toluol-4-sulfonyl)-β-D-galactopyranosid]；[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-6-methoxy-2-[(4-methylphenyl)sulfonyloxymethyl]oxan-3-yl] acetate
• CAS: 112716-28-6
• 化学式: C₂₀H₂₆O₁₁S
• 分子量: 474.486
• InChiKey: DYNSMQWMUMIXJH-LCWAXJCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-O-p-toluenesulfonyl-β-D-galactopyranoside 在 乙酸肼 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 52.5h， 生成 methyl 2,3,4-tri-O-acetyl-6-thio-6-[2'-(γ-butyrolactone)]-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Sialylmimetics as Rotavirus Inhibitors

  摘要：

  Rotaviruses cause severe gastroenteritis in infants and are estimated to be responsible for over 600 000 deaths annually, primarily in developing countries. The development of potential inhibitors of this virus is therefore of great interest, particularly since the safety and efficacy of rotaviral vaccines has recently been questioned. This study describes the synthesis of a variety of compounds that can be considered as mimetics of N-acetylneuraminic acid thioglycosides and the subsequent in vitro biological evaluation of these sialylmimetics as inhibitors of rotaviral infection. Our results show that readily accessible carbohydrate-based compounds have the potential to act as inhibitors of rotaviral replication in vitro, presumably through inhibition of the rotaviral adhesion process.

  DOI：

  10.1021/jm0100887
• 作为产物：
  描述：

  O1,O2,O3,O4-tetraacetyl-O6-(toluene-4-sulfonyl)-α-D-galactopyranose 在 氢溴酸 、 溶剂黄146 、 silver carbonate 作用下， 生成 methyl 2,3,4-tri-O-acetyl-6-O-p-toluenesulfonyl-β-D-galactopyranoside
  参考文献：
  名称：

  379.关于琼脂的研究。第二部分。从琼脂中分离3：6-脱水-1-半乳糖的衍生物并合成其对映体

  摘要：

  DOI：

  10.1039/jr9390001844

文献信息

• Synthesis of Positional Thiol Analogs of β-D-Galactopyranose
  作者：Zhichao Pei、Hai Dong、Rémi Caraballo、Olof Ramström

  DOI：10.1002/ejoc.200700364

  日期：2007.10

  Approaches toward the synthesis of thio- beta -D -galactose derivatives are described. These compounds were prepared from the parent carbohydrates: D-galactose, methyl P-D-galactoside and methyl P- ...

  描述了合成硫代-β-D-半乳糖衍生物的方法。这些化合物由母体碳水化合物制备：D-半乳糖、甲基 PD-半乳糖苷和甲基 P-...
• Haworth et al., Journal of the Chemical Society, 1940, p. 620,629
  作者：Haworth et al.

  DOI：——

  日期：——
• Synthesis of Novel Sialylmimetics as Biological Probes
  作者：Susan J. Bradley、Ashmath Fazli、Milton J. Kiefel、Mark von Itzstein

  DOI：10.1016/s0960-894x(01)00276-1

  日期：2001.6

  Glycomimetics are increasingly being recognised as powerful tools in the search for novel compounds that possess useful biological properties. This paper describes our preliminary efforts towards the development of novel mimetics of sialic acid thioglycosides. These sialylmimetics are readily prepared and have been shown, in some instances, to have biological properties similar to sialic acid thioglycosides. (C) 2001 Elsevier Science Ltd. All rights reserved.
• ‘Click chemistry’ synthesis of a library of 1,2,3-triazole-substituted galactose derivatives and their evaluation against Trypanosoma cruzi and its cell surface trans-sialidase
  作者：Ivone Carvalho、Peterson Andrade、Vanessa L. Campo、Paulo M.M. Guedes、Renata Sesti-Costa、João S. Silva、Sergio Schenkman、Simone Dedola、Lionel Hill、Martin Rejzek、Sergey A. Nepogodiev、Robert A. Field

  DOI：10.1016/j.bmc.2010.02.053

  日期：2010.4

  Trypanosoma cruzi trans-sialidase (TcTS) plays a key role in the recognition and invasion of host cells and in enabling the parasite to escape the human immune response. To explore this potential drug target, we have synthesized a small library of substrate analogues based on 1,4-disubstituted 1,2,3-triazole derivatives of galactose modified at either the C-1 or C-6 positions. This was achieved by coupling the appropriate azido-sugars with a panel of 23 structurally diverse terminal alkynes by using the copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) reaction, giving a library of 46 derivatives in good to excellent yield and with complete regioselectivity. The sugar triazoles showed weak inhibition towards TcTS-catalyzed hydrolysis of 2'-(4-methylumbelliferyl)-alpha-D-N-acetylneuraminic acid in vitro (<40% inhibition at 1 mM concentration); many of the compounds assessed proved to be acceptor substrates for the enzyme. Despite this modest inhibitory activity, in vitro trypanocidal activity assays against the trypomastigote form of T. cruzi Y strain revealed several compounds active in the low 100s of mu M range. Further assessment of these compounds against cultured mouse spleen cells suggests a specific mode of anti-parasite action rather than a generic cytotoxic effect. (C) 2010 Elsevier Ltd. All rights reserved.
• Haworth et al., Journal of the American Chemical Society, 1940, p. 620,629
  作者：Haworth et al.

  DOI：——

  日期：——