[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[3-cyano-4-(1H-indol-3-yl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridin-2-yl]sulfanyl]oxan-2-yl]methyl acetate | 844682-69-5

• 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,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[3-cyano-4-(1H-indol-3-yl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridin-2-yl]sulfanyl]oxan-2-yl]methyl acetate
• CAS: 844682-69-5
• 化学式: C₃₄H₃₇N₃O₉S
• 分子量: 663.748
• InChiKey: FSLQPRGKAMIDDZ-DAPGNZIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  192
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[3-cyano-4-(1H-indol-3-yl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridin-2-yl]sulfanyl]oxan-2-yl]methyl acetate 在 氨 作用下， 以 甲醇 为溶剂， 以90%的产率得到4-(1H-Indol-3-yl)-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-5,6,7,8,9,10-hexahydro-cycloocta[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：

  环辛酮 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 [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[3-cyano-4-(1H-indol-3-yl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridin-2-yl]sulfanyl]oxan-2-yl]methyl acetate
  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

文献信息

• A Total Synthesis of a New Class of Biazine Thioglycosides
  作者：Galal H. Elgemeie、Mona M. Hussein、Sheakha A. Al‐Khursani

  DOI：10.1081/car-200045262

  日期：2004.1

  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.