p-tolyl 3,4-di-O-benzoyl-1-thio-β-D-xylopyranoside | 1173995-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-tolyl 3,4-di-O-benzoyl-1-thio-β-D-xylopyranoside
• 英文别名: [(3R,4R,5R,6S)-4-benzoyloxy-5-hydroxy-6-(4-methylphenyl)sulfanyloxan-3-yl] benzoate
• CAS: 1173995-02-2
• 化学式: C₂₆H₂₄O₆S
• 分子量: 464.539
• InChiKey: KMOHEJWRRNQLEL-ONJIFJTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-tolyl 3,4-di-O-benzoyl-1-thio-β-D-xylopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 乙酰氯 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 12.08h， 生成 3β-O-(2-methyl-3,4-di-benzyl-O-α-D-xylopyranose)-22-O-benzylcholest-5,16-dien-29-ol
  参考文献：
  名称：

  Synthesis of analogues of linckoside B, a new neuritogenic steroid glycoside

  摘要：

  从冲绳海星 Linckia laevigata 中分离出的一种新的致神经甾体苷--linckoside B 的六种类似物（2-7）的简易合成方法已经开发成功。关键的类固醇苷元是通过二甲基氯化铝介导的 "烯 "反应生成的。通过施密特程序，使用三氯乙酰亚氨酸糖基供体构建糖苷键时，采用了一种多功能策略。

  DOI：

  10.1039/c3nj00514c
• 作为产物：
  描述：

  p-tolyl 1-thio-β-D-xylopyranose 、 氯化苄 在 二正丁基氧化锡 作用下， 以 苯 为溶剂， 以94%的产率得到p-tolyl 3,4-di-O-benzoyl-1-thio-β-D-xylopyranoside
  参考文献：
  名称：

  Facile synthesis of three bidesmosidic oleanolic acid saponins with strong inhibitory activity on pancreatic lipase

  摘要：

  The first synthesis of scabiosaponins E (1), F (2), and G (3), three new oleanolic acid saponins with strong inhibitory activity on pancreatic lipase isolated from the Chinese traditional medicinal herb Scabiosa tschiliensis, was efficiently achieved in an one-pot strategy under the combined use of glycosyl trichloro-acetimidates and p-toluene 1-thioglycosides (STol) as donors. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2009.04.024

文献信息

• Total Synthesis of Linckosides A and B, the Representative Starfish Polyhydroxysteroid Glycosides with Neuritogenic Activities
  作者：Dapeng Zhu、Biao Yu

  DOI：10.1021/jacs.5b11276

  日期：2015.12.9

  Linckosides A and B, two starfish metabolites with promising neuritogenic activities, are synthesized in a longest linear sequence of 32 steps and 0.5% overall yield; this represents the first synthesis of members of the polyhydroxysteroid glycoside family, which occur widely in starfishes.

  Linckosides A 和 B 是两种海星代谢物，具有良好的神经元活性，以最长的 32 步线性序列合成，总产率为 0.5%；这代表了广泛存在于海星中的多羟基类固醇糖苷家族成员的首次合成。
• Synthesis of Sea Cucumber Saponins with Antitumor Activities
  作者：Xiaofei Shao、Xiaobo Wang、Kaidi Zhu、Yongjun Dang、Biao Yu

  DOI：10.1021/acs.joc.0c01191

  日期：2020.10.2

  biological activities. Here, we report the synthesis of two representative congeners, namely, pervicoside B and C, starting from lanosterol with the longest linear sequence of both 34 steps and in 0.3% overall yields. The flexible synthetic approach has enabled us to expeditiously prepare 16 analogues for preliminary studies on the key structural features influencing their antiproliferative activities against

  甾烷糖苷是海参的特征代谢产物，具有多种生物活性。在这里，我们报告了两种代表性同类物的合成，即pervicoside B和C，它是从羊毛甾醇开始的，其线性最长的序列均为34个步骤，总产率为0.3％。灵活的合成方法使我们能够迅速制备出16种类似物，以初步研究影响其抗肿瘤细胞增殖活性的关键结构特征。发现简化的二糖与天然四糖一样有效，可用作未来研究的先导。
• Synthesis of analogues of linckoside B, a new neuritogenic steroid glycoside
  作者：Qingchao Liu、Yue Yu、Peng Wang、Yingxia Li

  DOI：10.1039/c3nj00514c

  日期：——

  A facile synthetic approach toward six designed analogues (2–7) of linckoside B, a new neuritogenic steroid glycoside isolated from the Okinawan starfish Linckia laevigata, has been developed. The key steroid aglycon was achieved by a dimethylaluminum chloride-mediated ‘ene’ reaction. A versatile strategy was employed for the construction of glycosidic bonds through Schmidt's procedure using a glycosyl trichloroacetimidate donor.

  从冲绳海星 Linckia laevigata 中分离出的一种新的致神经甾体苷--linckoside B 的六种类似物（2-7）的简易合成方法已经开发成功。关键的类固醇苷元是通过二甲基氯化铝介导的 "烯 "反应生成的。通过施密特程序，使用三氯乙酰亚氨酸糖基供体构建糖苷键时，采用了一种多功能策略。
• Facile synthesis of three bidesmosidic oleanolic acid saponins with strong inhibitory activity on pancreatic lipase
  作者：Tiantian Guo、Qingchao Liu、Peng Wang、Lei Zhang、Wei Zhang、Yingxia Li

  DOI：10.1016/j.carres.2009.04.024

  日期：2009.7

  The first synthesis of scabiosaponins E (1), F (2), and G (3), three new oleanolic acid saponins with strong inhibitory activity on pancreatic lipase isolated from the Chinese traditional medicinal herb Scabiosa tschiliensis, was efficiently achieved in an one-pot strategy under the combined use of glycosyl trichloro-acetimidates and p-toluene 1-thioglycosides (STol) as donors. (C) 2009 Published by Elsevier Ltd.