methyl 2,3,4-tri-O-acetyl-6-deoxy-6-thioacetyl-β-D-glucopyranoside | 19204-80-9

• 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: methyl 2,3,4-tri-O-acetyl-6-deoxy-6-thioacetyl-β-D-glucopyranoside
• 英文别名: methyl 2,3,4-tri-O-acetyl-6-thiolacetyl-β-D-glucopyranoside；methyl 6-S-acetyl-2,3,4-tri-O-acetyl-β-D-glucopyranoside；Methyl-2,3,4-tri-O-acetyl-6-S-acetyl-6-deoxy-6-thio-β-D-glucopyranosid；[(2S,3S,4S,5R,6R)-4,5-diacetyloxy-2-(acetylsulfanylmethyl)-6-methoxyoxan-3-yl] acetate
• CAS: 19204-80-9
• 化学式: C₁₅H₂₂O₉S
• 分子量: 378.4
• InChiKey: KGPJKVYHVUTECA-UXXRCYHCSA-N

物化性质

• 熔点：
  94.5 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 沸点：
  435.5±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

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 2,3,4-tri-O-acetyl-6-deoxy-6-thioacetyl-β-D-glucopyranoside 在 乙酸肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成
  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：

  甲基6-O-[(4-甲基苯基)磺酰基]-beta-D-吡喃葡萄糖苷 在 吡啶 作用下， 以 丙酮 为溶剂， 反应 63.0h， 生成 methyl 2,3,4-tri-O-acetyl-6-deoxy-6-thioacetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Novel Sialylmimetics as Biological Probes

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(01)00276-1

文献信息

• Synthetic sulfoglycolipids targeting the serine–threonine protein kinase Akt
  作者：Barbara Costa、Milind Dangate、Maria Vetro、Giulia Donvito、Luca Gabrielli、Loredana Amigoni、Giuliana Cassinelli、Cinzia Lanzi、Michela Ceriani、Luca De Gioia、Giulia Filippi、Laura Cipolla、Nadia Zaffaroni、Paola Perego、Diego Colombo

  DOI：10.1016/j.bmc.2016.05.031

  日期：2016.8

  The serine–threonine protein kinase Akt, also known as protein kinase B, is a key component of the phosphoinositide 3-kinase (PI3K)–Akt–mTOR axis. Deregulated activation of this pathway is frequent in human tumors and Akt-dependent signaling appears to be critical in cell survival. PI3K activation generates 3-phosphorylated phosphatidylinositols that bind Akt pleckstrin homology (PH) domain. The blockage

  丝氨酸-苏氨酸蛋白激酶Akt，也称为蛋白激酶B，是磷酸肌醇3激酶（PI3K）-Akt-mTOR轴的关键组成部分。该途径的失活激活在人类肿瘤中很常见，依赖Akt的信号传导似乎对细胞存活至关重要。PI3K激活产生3-磷酸化磷脂酰肌醇，该蛋白结合Akt普列克蛋白同源性（PH）域。Akt PH域/磷酸肌醇相互作用的阻断代表了一种有希望的方法来干扰过度活化的Akt的致癌潜力。在本研究中，已经合成了基于β-葡萄糖苷支架的磷脂酰肌醇模拟物作为Akt抑制剂。该化合物在葡萄糖的异头位置具有一个或两个不同长度的亲脂性部分，并在C-6处具有酸性或碱性基团。对接研究ø -octadecanoyl -2- ö -β- d -sulfoquinovopyranosyl- SN -甘油作为合成的化合物中最好的Akt抑制剂，其可被视为用于在Akt的抑制剂的设计进一步优化的引线。
• A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light To Synthesize Deoxyglycosides
  作者：Jian-Tao Ge、Lang Zhou、Tao Luo、Jian Lv、Hai Dong

  DOI：10.1021/acs.orglett.9b02033

  日期：2019.8.2

  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.