Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-cyano-4-pyridin-3-yl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester | 844681-95-4

• 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: Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-cyano-4-pyridin-3-yl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(3-cyano-4-pyridin-3-yl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-2-yl)sulfanyl]oxan-2-yl]methyl acetate
• CAS: 844681-95-4
• 化学式: C₃₀H₃₃N₃O₉S
• 分子量: 611.673
• InChiKey: NOMRWLAPRLOSKT-JGALVPIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 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-4-pyridin-3-yl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester 在 氨 作用下， 以 甲醇 为溶剂， 以85%的产率得到4-Pyridin-3-yl-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-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：

  2-cyano-3-(3'-pyridyl)acrylthioamide 在 乙酸铵 、 硫酸氢铵 、 六甲基二硅氮烷 作用下， 以 乙醇 为溶剂， 反应 51.0h， 生成 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-cyano-4-pyridin-3-yl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-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