methyl 6-O-p-tolylsulfonyl-β-D-galactopyranoside | 57817-52-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-p-tolylsulfonyl-β-D-galactopyranoside
• 英文别名: methyl 6-O-tosyl-β-D-galactopyranoside；Methyl-α-D-galactopyranosido-6-p-toluol-sulfonat；methyl-[O⁶-(toluene-4-sulfonyl)-β-D-galactopyranoside]；Methyl-[O⁶-(toluol-4-sulfonyl)-β-D-galactopyranosid]；Methyl 6-O-tosyl-beta-D-galactopyranoside；[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 57817-52-4
• 化学式: C₁₄H₂₀O₈S
• 分子量: 348.374
• InChiKey: DBMMVDKCWRGJEG-MBJXGIAVSA-N

物化性质

• 熔点：
  137 °C
• 沸点：
  550.2±50.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.85
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  122.52
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 6-O-p-tolylsulfonyl-β-D-galactopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以93%的产率得到methyl 3,6-anhydro-β-D-galactopyranoside
  参考文献：
  名称：

  TBAF影响由6-O-甲苯磺酰基吡喃糖苷形成3,6-脱水。

  摘要：

  3,6-脱水糖是藻类多糖中的常见结构，并存在于呋喃达克丁和sauropunol天然产物中。我们发现用氟化四丁基铵处理6-O-甲苯磺酰基吡喃糖苷提供了温和的，高产率的3，6-脱水糖的合成。使用O-糖苷底物，分离出3，6-脱水吡喃糖苷，并且使用N，O-二甲基羟胺糖苷产生3，6-脱水呋喃糖苷。据报道，采用这种方法，可以合成几种3,6-脱水糖天然产物的简捷合成路线，包括呋喃果苦碱A和sauropunols AD。

  DOI：

  10.1021/acs.orglett.0c00045
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-O-(p-tolylsulfonyl)-β-D-galactopyranose 在 甲醇 、 氢溴酸 、 sodium 、 溶剂黄146 、 silver carbonate 作用下， 生成 methyl 6-O-p-tolylsulfonyl-β-D-galactopyranoside
  参考文献：
  名称：

  Haworth et al., Journal of the Chemical Society, 1940, p. 620,629

  摘要：

  DOI：

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-...
• S-Acetyl migration in synthesis of sulfur-containing glycosides
  作者：Yixuan Zhou、Xiaoling Zhang、Bo Ren、Bin Wu、Zhichao Pei、Hai Dong

  DOI：10.1016/j.tet.2014.07.014

  日期：2014.9

  Unexpected products are often found in the synthesis of sulfur-containing glycosides where the sulfur-containing group is acquired through substitution of a leaving group by a thioacetate reagent. Thus low yields have to be born. The reason has been disclosed to originate from the basicity and nucleophilicity of sulfur atom leading to a thioacetyl group migration in this study. The migration may occur

  在含硫糖苷的合成中经常发现意外的产物，其中含硫基团是通过用硫代乙酸盐试剂取代离去基团而获得的。因此必须产生低产量。在本研究中，已公开原因是由于硫原子的碱性和亲核性导致硫代乙酰基迁移。可能通过五元或六元环四面体中间体发生迁移，然后裂解该中间体的CS键以形成巯基阴离子，然后另一个乙酰基从硫代乙酸盐试剂迁移至巯基阴离子，从而导致意外的产物乙酰化的邻近羟基。迁移的发生可能取决于硫代乙酸盐试剂的浓度以及底物本身的空间和立体电子效应。基于这些结果，可以大大提高合成含硫糖苷的产率。
• Synthesis and Biological Evaluation of Sialylmimetics as Rotavirus Inhibitors
  作者：Ashmath Fazli、Susan J. Bradley、Milton J. Kiefel、Clare Jolly、Ian H. Holmes、Mark von Itzstein

  DOI：10.1021/jm0100887

  日期：2001.9.1

  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.
• 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.