Acetic acid (2R,3S,4S,5R,6S)-5-acetoxy-2-acetoxymethyl-4-azido-6-ethylsulfanyl-tetrahydro-pyran-3-yl ester | 345197-29-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4S,5R,6S)-5-acetoxy-2-acetoxymethyl-4-azido-6-ethylsulfanyl-tetrahydro-pyran-3-yl ester
• 英文别名: ethyl 2,4,6-tri-O-acetyl-3-deoxy-3-azido-1-thio-β-D-glucopyranoside
• CAS: 345197-29-7
• 化学式: C₁₄H₂₁N₃O₇S
• 分子量: 375.403
• InChiKey: SFMASDLVQHRLDS-ITGHMWBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  136.89
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4S,5R,6S)-5-acetoxy-2-acetoxymethyl-4-azido-6-ethylsulfanyl-tetrahydro-pyran-3-yl ester 在 sodium methylate 、 sodium hydride 作用下， 生成 Phosphoric acid (2R,3R,4S,5S,6R)-4-azido-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester dibenzyl ester
  参考文献：
  名称：

  Expanding the Pyrimidine Diphosphosugar Repertoire: The Chemoenzymatic Synthesis of Amino- and Acetamidoglucopyranosyl Derivatives

  摘要：

  The exploitation of a unique thymidylyltransferase (Ep ) allows the rapid syntheses of thymidine and uridine 5'-(aminodeoxy-α-D-hexopyranosyl diphosphates), 5'-(acetamidodeoxy-α-D-hexopyranosyl diphosphates), and even 5'-(aminodideoxy-α-D-hexopyranosyl diphosphates), which are amino analogues of the products from the native reaction of Ep .

  DOI：

  10.1002/1521-3773(20010417)40:8<1502::aid-anie1502>3.0.co;2-k
• 作为产物：
  描述：

  (乙基硫代)三甲基硅烷 、 1,2,4,6-tetra-O-acetyl-3-azido-3-deoxy-D-glucopyranose 在 zinc(II) iodide 作用下， 以84.2%的产率得到Acetic acid (2R,3S,4S,5R,6S)-5-acetoxy-2-acetoxymethyl-4-azido-6-ethylsulfanyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Expanding the Pyrimidine Diphosphosugar Repertoire: The Chemoenzymatic Synthesis of Amino- and Acetamidoglucopyranosyl Derivatives

  摘要：

  The exploitation of a unique thymidylyltransferase (Ep ) allows the rapid syntheses of thymidine and uridine 5'-(aminodeoxy-α-D-hexopyranosyl diphosphates), 5'-(acetamidodeoxy-α-D-hexopyranosyl diphosphates), and even 5'-(aminodideoxy-α-D-hexopyranosyl diphosphates), which are amino analogues of the products from the native reaction of Ep .

  DOI：

  10.1002/1521-3773(20010417)40:8<1502::aid-anie1502>3.0.co;2-k

文献信息

• Automated access to well-defined ionic oligosaccharides
  作者：Yuntao Zhu、Theodore Tyrikos-Ergas、Kevin Schiefelbein、Andrea Grafmüller、Peter H. Seeberger、Martina Delbianco

  DOI：10.1039/d0ob00137f

  日期：——

  Ionic polysaccharides are part of many biological events, but lack structural characterisation due to challenging purifications and complex synthesis. Four monosaccharides bearing modifications not found in nature are used for the automated synthesis of a collection of ionic oligosaccharides. Structural analysis reveals how the charge pattern affects glycan conformation.

  离子多糖是许多生物学事件的一部分，但是由于具有挑战性的纯化和复杂的合成，因此缺乏结构表征。四种在自然界中未发现的带有修饰的单糖用于自动合成一系列离子寡糖。结构分析揭示了电荷模式如何影响聚糖构象。