Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-cyano-4-(1H-indol-3-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-2-ylsulfanyl]-tetrahydro-pyran-3-yl ester | 844682-59-3

• 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-4-(1H-indol-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-(1H-indol-3-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-2-yl]sulfanyl]oxan-2-yl]methyl acetate
• CAS: 844682-59-3
• 化学式: C₃₃H₃₅N₃O₉S
• 分子量: 649.722
• InChiKey: KZWXQZYCLPURLJ-QRRWAWJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-cyano-4-(1H-indol-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79%的产率得到4-(1H-Indol-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：

  (Z)-2-cyano-3-(1H-indol-3-yl)prop-2-enethioamide 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-4-(1H-indol-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