(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((4-methoxyphenyl)ethynyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1467024-09-4

• 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: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((4-methoxyphenyl)ethynyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• 英文别名: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[(4-methoxyphenyl)ethynyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1467024-09-4
• 化学式: C₂₃H₂₆O₁₀S
• 分子量: 494.519
• InChiKey: PZBSLLPHVPWMGS-ZQGJOIPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  (4-甲氧基苯乙炔基)三甲基硅烷 在 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.06h， 生成 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((4-methoxyphenyl)ethynyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Continuous-flow processes for the S-alkynylation of cysteine-containing peptides and thioglycosides under catalyst-free, oxidant-free and mild conditions

  摘要：

  含半胱氨酸肽和1-硫代糖苷残基的选择性S-炔基化反应已经在连续流条件下开发。

  DOI：

  10.1039/d1gc01937f

文献信息

• Stereoselective Palladium-Catalyzed Alkenylation and Alkynylation of Thioglycosides
  作者：Etienne Brachet、Jean-Daniel Brion、Mouad Alami、Samir Messaoudi

  DOI：10.1002/adsc.201300419

  日期：2013.9.16

  An efficient and unprecedented palladium‐catalyzed S‐glycosylation reaction of a range of alkenyl and alkynyl halides by using thiosugars as nucleophile partners has been established. With palladium diacetate in combination with Xantphos as the catalytic system, a variety of β‐alkenylthioglycosides as well as β‐alkynylthioglycosides can be prepared in good to excellent yields. The efficiency of this

  通过使用硫糖作为亲核试剂的伙伴，已经建立了有效且前所未有的钯催化的一系列链烯基和炔基卤化物的S-糖基化反应。将二乙酸钯与Xantphos结合用作催化体系，可以制备各种β-烯基硫代糖苷以及β-炔基硫代糖苷，而且收率很高。叶片封闭的β-葡萄糖苷酶抑制剂的正式合成充分证明了该通用方案的有效性。
• 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。
• Photochemical Dual-Catalytic Synthesis of Alkynyl Sulfides
  作者：Jeffrey Santandrea、Clémentine Minozzi、Corentin Cruché、Shawn K. Collins

  DOI：10.1002/anie.201705903

  日期：2017.9.25

  Catalytic partnership: A photochemical dual-catalytic cross-coupling to form alkynyl sulfides through C(sp)−S bond formation is promoted by a carbazole-based photocatalyst using continuous flow techniques in short reaction times (50–96 %, 30 min). In addition, incorporation of an alkynyl sulfide functional group into a macrocyclic scaffold was demonstrated as the first application of photoredox/nickel

  催化伙伴关系：基于咔唑的光催化剂采用连续流动技术在较短的反应时间（50-96％，30分钟）内促进了光化学双催化交叉偶联，通过C（sp）-S键形成炔基硫化物。另外，作为大环环化的光氧化还原/镍双重催化的首次应用，证明了将炔基硫醚官能团结合到大环支架中。