Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-cyano-5,6,7,8-tetrahydro-[4,4']biquinolinyl-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester | 844682-41-3

• 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,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-cyano-5,6,7,8-tetrahydro-[4,4']biquinolinyl-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(3-cyano-4-quinolin-4-yl-5,6,7,8-tetrahydroquinolin-2-yl)sulfanyl]oxan-2-yl]methyl acetate
• CAS: 844682-41-3
• 化学式: C₃₃H₃₃N₃O₉S
• 分子量: 647.706
• InChiKey: ABSXUWVMRRGYTR-QRRWAWJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  189
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-cyano-5,6,7,8-tetrahydro-[4,4']biquinolinyl-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester 在 氨 作用下， 以 甲醇 为溶剂， 以80%的产率得到2-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-5,6,7,8-tetrahydro-[4,4']biquinolinyl-3-carbonitrile
  参考文献：
  名称：

  A Total Synthesis of a New Class of Biazine Thioglycosides

  摘要：

  A new method for the synthesis of bipyridinyl S-glycosides 11 and 12 has provided the title compounds in a higher yield. Application of a one-pot glycosylation methodology resulted in an efficient, high-yield synthesis of biazine S-glycosides 17-20 An X-ray diffraction analysis of 11 disclosed the conformation of this glycoside as the S-glycoside and not the corresponding N-form.

  DOI：

  10.1081/car-200045262
• 作为产物：
  描述：

  quinoline-4-ylmethylidenecyanothioacetamide 在 ammonium acetate 氢氧化钾 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-cyano-5,6,7,8-tetrahydro-[4,4']biquinolinyl-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  A Total Synthesis of a New Class of Biazine Thioglycosides

  摘要：

  A new method for the synthesis of bipyridinyl S-glycosides 11 and 12 has provided the title compounds in a higher yield. Application of a one-pot glycosylation methodology resulted in an efficient, high-yield synthesis of biazine S-glycosides 17-20 An X-ray diffraction analysis of 11 disclosed the conformation of this glycoside as the S-glycoside and not the corresponding N-form.

  DOI：

  10.1081/car-200045262