Acetic acid (2S,3R,4S,5S,6R)-3,5-diacetoxy-2-mercapto-6-methyl-tetrahydro-pyran-4-yl ester | 56981-48-7

• 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: Acetic acid (2S,3R,4S,5S,6R)-3,5-diacetoxy-2-mercapto-6-methyl-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3S,4S,5R,6S)-4,5-diacetyloxy-2-methyl-6-sulfanyloxan-3-yl] acetate
• CAS: 56981-48-7
• 化学式: C₁₂H₁₈O₇S
• 分子量: 306.337
• InChiKey: BWMDVFOFYSJKHO-UOORRKKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.13
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4S,5S,6R)-3,5-diacetoxy-2-mercapto-6-methyl-tetrahydro-pyran-4-yl ester 、 imino(2-iodophenyl)(trifluoromethyl)-λ⁶-sulfanone 在 palladium [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine-κP](methanesulfonato-κO) 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以78%的产率得到2-methyl-6-((2-(S-(trifluoromethyl)sulfonimidoyl)phenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  钯催化的 Migita Cross-Couling 合成 S-三氟甲基 S-芳基亚砜亚胺硫糖苷

  摘要：

  已经报道了合成 S-三氟甲基 S-芳基亚砜亚胺硫糖苷的通用方案。该协议基于邻碘 S-三氟甲基 S-芳基亚砜亚胺和多种 1-硫糖之间的 Pd 催化 Migita 交叉偶联。该方法可以以中等至良好的收率获得一系列功能化的 S-三氟甲基 S-芳基亚砜亚胺硫糖苷。此外，两种非对映异构体都可以通过简单的结晶或 HPLC 轻松分离，并且提供了每种纯三氟甲基亚砜亚胺的完整表征。

  DOI：

  10.1002/ejoc.202000821

文献信息

• Electrochemical nickel-catalyzed Migita cross-coupling of 1-thiosugars with aryl, alkenyl and alkynyl bromides
  作者：Mingxiang Zhu、Mouad Alami、Samir Messaoudi

  DOI：10.1039/d0cc01126f

  日期：——

  Here we report a simple route towards the synthesis of thioglycosides, in which electrochemical cross-coupling is used to form a S-C glycosidic bond from protected and unprotected thiosugars with functionalized aryl bromides under base free conditions. The reaction manifold that we report here demonstrates the power of electrochemistry to access highly complex glycosides under mild conditions.

  在这里，我们报告了一种简单的合成硫糖苷的方法，其中电化学交叉偶联用于在无碱条件下由受保护和未受保护的硫糖与功能化的芳基溴化物形成SC糖苷键。我们在此报告的反应歧管证明了在温和条件下电化学作用可获取高度复杂的糖苷的能力。
• <scp>Togni‐II</scp> Reagent Mediated Selective Hydrotrifluoromethylation and Hydrothiolation of Alkenes ^†
  作者：Shuang Teng、Lingkui Meng、Bingbing Xu、Guangsheng Tu、Peng Wu、Zhiwen Liao、Yulin Tan、Jian Guo、Jing Zeng、Qian Wan

  DOI：10.1002/cjoc.202100464

  日期：2021.12

  reactions of Togni-II reagent and thiols, a thiol-tuned selective functionalization of unactivated olefins was disclosed. In combination with aryl thiols, stoichiometric amount of Togni-II reagent prompted a hydrotrifluoromethylation of alkenes, in which, aryl thiols played as reductant and hydrogen source; while by utilization of alkyl thiols, catalytic amount of Togni-II reagent initiated thiol-ene

  基于 Togni-II 试剂和硫醇的氧化还原反应，公开了未活化烯烃的硫醇调节的选择性官能化。与芳基硫醇结合，化学计量的Togni-II试剂促进烯烃的氢三氟甲基化，其中芳基硫醇作为还原剂和氢源；而通过利用烷基硫醇，催化量的Togni-II试剂引发硫醇-烯和硫醇-炔反应。报告的应用程序的特点是它们的操作简单和广泛的官能团耐受性。
• Ni/Photoredox-Dual-Catalyzed Functionalization of 1-Thiosugars
  作者：Mingxiang Zhu、Guillaume Dagousset、Mouad Alami、Emmanuel Magnier、Samir Messaoudi

  DOI：10.1021/acs.orglett.9b01730

  日期：2019.7.5

  A general protocol for functionalization of glycosyl thiols has been reported. This protocol is based on a single-electron Ni/photoredox dual-catalyzed cross coupling between 1-thiosugars and a broad range of aryl bromides and iodides as well as alkenyl and alkynyl halides. This base-free method gives access to a series of functionalized thioglycosides in moderate to excellent yields with a perfect control of the anomeric configuration. Moreover, it has been shown that this methodology may be transposed successfully to the continuous-flow photoredox chemistry.