(3S)-deoxypumiloside tetraacetate | 184916-42-5

• 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: (3S)-deoxypumiloside tetraacetate
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(1S,18S,19R,20S)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-2,4,6,8,10,15-hexaen-18-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 184916-42-5
• 化学式: C₃₄H₃₆N₂O₁₂
• 分子量: 664.666
• InChiKey: WAJNXYSUFIVUGE-XLOZJSMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  166
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (3S)-deoxypumiloside tetraacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以44%的产率得到(3S)-deoxypumiloside
  参考文献：
  名称：

  Camptothecin-related alkaloids from hairy roots of Ophiorrhiza pumila

  摘要：

  Hairy roots of Ophiorrhiza pumila, a rubiaceous camptothecin-producing plant, were obtained. From an investigation of the secondary metabolites, it was found that the hairy roots produced camptothecin and its related alkaloids, i.e. (3S)-pumiloside, (3S)- and (3R)-deoxypumilosides and strictosamide. We also isolated two new camptothecinoids, OPHR-23 and OPHR-17, the structures of which including the absolute configurations, were determined by spectroscopic analyses and chemical conversion from tryptamine and secologanin. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01196-1
• 作为产物：
  描述：

  异长春花苷内酰胺 在 吡啶 、 palladium diacetate 、 sodium periodate 、 甲酸 、 1,1'-bis(diphenylphosphino)ferrocene 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 六甲基磷酰三胺 为溶剂， 生成 (3S)-deoxypumiloside tetraacetate
  参考文献：
  名称：

  3（R）-和3（S）-脱氧腰果糖苷的分离和部分合成；喜树碱生产厂Ophiorrhiza pumila的关键代谢物的结构修订

  摘要：

  在喜树碱代谢物的来源植物Ophiorrhiza pumila（Rubiaceae）中发现了C-3的3（R）-和3（S）-脱氧普米洛甙对映体对。这些结构通过光谱分析和部分立体选择性合成得到证实。先前报道的“脱氧油苷”在C-3处的构型从3（S）修订为3（R）。

  DOI：

  10.1016/s0040-4039(97)00858-7

文献信息

• Isolation and partial synthesis of 3(R)- and 3(S)-deoxypumiloside; structural revision of the key metabolite from the camptothecin producing plant, Ophiorrhiza pumila
  作者：Mariko Kitajima、Seiji Masumoto、Hiromitsu Takayama、Norio Aimi

  DOI：10.1016/s0040-4039(97)00858-7

  日期：1997.6

  the C-3 epimeric pair of 3(R)- and 3(S)-deoxypumiloside were found in Ophiorrhiza pumila (Rubiaceae), a source plant of camptothecinoid metabolites. These structures were confirmed by spectroscopic analysis and partial stereoselective syntheses. The configuration at C-3 of the previously reported “deoxypumiloside” is revised to 3(R) from 3(S).

  在喜树碱代谢物的来源植物Ophiorrhiza pumila（Rubiaceae）中发现了C-3的3（R）-和3（S）-脱氧普米洛甙对映体对。这些结构通过光谱分析和部分立体选择性合成得到证实。先前报道的“脱氧油苷”在C-3处的构型从3（S）修订为3（R）。
• Camptothecin-related alkaloids from hairy roots of Ophiorrhiza pumila
  作者：Mariko Kitajima、Satoshi Yoshida、Kyoko Yamagata、Mio Nakamura、Hiromitsu Takayama、Kazuki Saito、Hiroko Seki、Norio Aimi

  DOI：10.1016/s0040-4020(02)01196-1

  日期：2002.11

  Hairy roots of Ophiorrhiza pumila, a rubiaceous camptothecin-producing plant, were obtained. From an investigation of the secondary metabolites, it was found that the hairy roots produced camptothecin and its related alkaloids, i.e. (3S)-pumiloside, (3S)- and (3R)-deoxypumilosides and strictosamide. We also isolated two new camptothecinoids, OPHR-23 and OPHR-17, the structures of which including the absolute configurations, were determined by spectroscopic analyses and chemical conversion from tryptamine and secologanin. (C) 2002 Elsevier Science Ltd. All rights reserved.