methyl 2,3,5-tri-O-acetyl-6-S-acetyl-6-thio-β-D-galactopyranoside | 183137-19-1

• 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: methyl 2,3,5-tri-O-acetyl-6-S-acetyl-6-thio-β-D-galactopyranoside
• 英文别名: methyl 2,3,4-tri-O-acetyl-6-thiolacetyl-β-D-galactopyranoside；methyl 2,3,4-tri-O-acetyl-6-(S)-acetyl-β-D-galactopyranoside；methyl 6-S-acetyl-2,3,4-tri-O-acetyl-β-D-galactopyranoside；[(2S,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetylsulfanylmethyl)-6-methoxyoxan-3-yl] acetate
• CAS: 183137-19-1
• 化学式: C₁₅H₂₂O₉S
• 分子量: 378.4
• InChiKey: KGPJKVYHVUTECA-GZBLMMOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 2,3,5-tri-O-acetyl-6-S-acetyl-6-thio-β-D-galactopyranoside 在 一水合肼 、 三(2-羰基乙基)磷盐酸盐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.03h， 以85%的产率得到Methyl 2,3,4-Tri-O-acetyl-6-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light To Synthesize Deoxyglycosides

  摘要：

  We herein developed an efficient method for removing thioacetyl to synthesize acylated deoxy glycosides in a one-pot reaction, where the thioacetyl was selectively deacetylated by hydrazine hydrate in DMF within 2-5 min at room temperature, followed by desulfurization under UV light for 1-2 h in the presence of TCEP center dot HCl. The method was then used to synthesize 2-deoxy glycosides with absolute alpha/beta-configuration via stereoselective control of C-2 thioacetate in glycosylation.

  DOI：

  10.1021/acs.orglett.9b02033
• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 吡啶 作用下， 以 丙酮 为溶剂， 反应 66.5h， 生成 methyl 2,3,5-tri-O-acetyl-6-S-acetyl-6-thio-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

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-...
• Synthesis of Deoxyglycosides by Desulfurization under UV Light
  作者：Jian-Tao Ge、Ying-Ying Li、Jun Tian、Rong-Zhen Liao、Hai Dong

  DOI：10.1021/acs.joc.7b00896

  日期：2017.7.7

  performed to develop a highly efficient method whereby desulfurization could be completed in 0.5 h under ultraviolet light, at room temperature, and in the presence of trialkylphosphine. Using this method, deoxyglycosides could be produced from sulfur-containing glycosides in almost quantitative yields. The much higher reactivity of desulfurization with triethylphosphine versus that with triethylphosphite

  进行这项研究是为了开发一种高效的方法，该方法可以在紫外线，室温，三烷基膦的存在下于0.5小时内完成脱硫。使用这种方法，可以几乎定量地从含硫糖苷生产脱氧糖苷。还讨论了用三乙基膦进行脱硫的反应性比用亚磷酸三乙酯进行脱硫的反应性高得多。
• 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.