2,3,5-tri-O-acetyl-α-L-arabinofuranosyl trichloroacetimidate | 335591-65-6

• 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: 2,3,5-tri-O-acetyl-α-L-arabinofuranosyl trichloroacetimidate
• 英文别名: [(2S,3S,4R,5S)-3,4-diacetyloxy-5-(2,2,2-trichloroethanimidoyl)oxyoxolan-2-yl]methyl acetate
• CAS: 335591-65-6
• 化学式: C₁₃H₁₆Cl₃NO₈
• 分子量: 420.631
• InChiKey: KKCXVRZXKFWOED-MMWGEVLESA-N

物化性质

• 沸点：
  415.3±55.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-acetyl-α-L-arabinofuranosyl trichloroacetimidate 在 sodium hydroxide 、 4 A molecular sieve 、 三氟化硼乙醚 、 水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 重楼皂苷I
  参考文献：
  名称：

  Synthesis of three diosgenyl saponins: dioscin, polyphyllin D, and balanitin 7

  摘要：

  Dioscin, polyphyllin D, and balanitin 7, which belong to a group of structurally similar diosgenyl saponins with promising bioactivities, were synthesized by stepwise glycosylation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00066-x
• 作为产物：
  描述：

  1,2,3,5-tetra-O-acetyl-L-arabinofuranose 在 氢溴酸 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2,3,5-tri-O-acetyl-α-L-arabinofuranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of three diosgenyl saponins: dioscin, polyphyllin D, and balanitin 7

  摘要：

  Dioscin, polyphyllin D, and balanitin 7, which belong to a group of structurally similar diosgenyl saponins with promising bioactivities, were synthesized by stepwise glycosylation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00066-x

文献信息

• Synthesis of novel diosgenyl saponin analogs and evaluation effects of rhamnose moeity on their cytotoxic activity
  作者：Xin Meng、Yiwu Pan、Tao Liu、Chen Luo、Shuli Man、Yongmin Zhang、Yan Zhang

  DOI：10.1016/j.carres.2021.108359

  日期：2021.8

  type of natural products derived from plants, are the main active component of traditional chinese medicine. Inspiringly, a large number of natural diosgensyl saponins have been shown to exert excellent toxicity to hepatocellular cancer (HCC) cells. In order to better understand the relationship between the structures and their biological effects, a group of diosgenyl saponins (1–4 as natural products

  薯蓣皂苷是一类从植物中提取的天然产物，是中药的主要活性成分。令人鼓舞的是，大量天然薯蓣皂苷已被证明对肝细胞癌细胞（HCC）具有极好的毒性。为了更好地理解其结构与其生物效应之间的关系，高效合成了一组薯蓣皂苷（ 1-4为天然产物， 5和6为其类似物）。在人肝细胞癌 (HepG2) 细胞上评估了这些化合物的细胞毒活性。构效关系研究表明，五糖或六糖皂苷类似物的活性比相应的二糖类似物或薯蓣皂苷的活性相对较低。这些皂苷上4支链鼠李糖部分的延伸对其细胞毒活性没有表现出明显的影响，这表明一定数量的鼠李糖部分和连接方式可以影响类固醇皂苷对HepG2细胞的细胞毒性。
• Synthesis of the Highly Glycosylated Hydrophilic Motif of Extensins
  作者：Akihiro Ishiwata、Sophon Kaeothip、Yoichi Takeda、Yukishige Ito

  DOI：10.1002/anie.201404904

  日期：2014.9.8

  stereoselective synthesis of one of the highly glycosylated motifs, Ser(Galp1)‐Hyp(Araf4)‐Hyp(Araf4)‐Hyp(Araf3)‐Hyp(Araf1). The synthesis has been completed by the application of 2‐(naphthyl)methylether‐mediated intramolecular aglycon delivery to the stereoselective construction of the Ser(Galp1) and Hyp(Arafn) fragments as the key step, as well as Fmoc solid‐phase peptide synthesis for the backbone

  Extensin是植物细胞外基质蛋白的结构基序，具有独特的高度糖基化，亲水性和重复性Ser 1 Hyp 4五肽单元，已被提议包括脯氨酸残基的翻译后羟基化和随后的寡L-阿拉伯糖基化羟基脯氨酸的合成以及丝氨酸残基的半乳糖基化。本文报道了一种高度糖基化的基序之一Ser（Galp 1）-Hyp（Araf 4）-Hyp（Araf 4）-Hyp（Araf 3）-Hyp（Araf 1）的立体选择性合成）。通过将2-（萘基）甲醚介导的分子内糖苷配基传递应用于Ser（Galp 1）和Hyp（Araf n）片段的立体选择性构建以及Fmoc固相，完成了合成肽合成为主链五肽。
• 一种玫瑰红景天活性成分络塞维或洛塞啉的合成方法
  申请人：天圆（宁波）生物医药科技有限公司

  公开号：CN110590872A

  公开（公告）日：2019-12-20

  本发明提供了一种玫瑰红景天活性成分络塞维或洛塞啉的合成方法。本发明采用汇聚合成策略，以rosin为起始原料，通过保护与去保护策略将其改造为糖受体，之后分别与阿拉伯吡喃糖以及阿拉伯呋喃糖形成的糖供体在促进剂存在下，快速高效地合成得到rosavin及rosarin。本发明涉及的合成方法原料便宜易得，反应条件温和，所得产物纯度高，相比目前报道的线性合成策略更具优势，具有非常好的工业化前景。
• Synthesis and antitumor activity of new shikonin glycosides
  作者：Yehua Su、Jiansheng Xie、Yanguang Wang、Xun Hu、Xianfu Lin

  DOI：10.1016/j.ejmech.2010.02.002

  日期：2010.7

  Eleven shikonin glycosides were synthesized and evaluated for their antitumor activity in vitro. Some of them were found to exhibit cytotoxic activities against both drug sensitive cell lines (K562, MCF-7 and HL60) and their drug resistant cell sublines (K562/ADR, MCF-7/ADR and HL60/ADR). (C) 2010 Published by Elsevier Masson SAS.
• Fluorophore-Appended Steroidal Saponin (Dioscin and Polyphyllin D) Derivatives
  作者：Zhiqi Yang、Ella Lai-Ming Wong、Tina Yuen-Ting Shum、Chi-Ming Che、Yongzheng Hui

  DOI：10.1021/ol0475616

  日期：2005.2.1

  The synthesis of three fluorophore-appended derivatives of dioscin and polyphyllin D is reported herein. Starting from trillin, dansyl derivatives A-C were prepared in overall yields of 7-12% over 7-10 steps. A study of their behavior in a variety of polar solvents suggests that dansyl derivatives A-C are capable of micellar self-assembly and can maintain cytotoxicities (IC50 = 15-18 muM) against the HeLa carcinoma cell line evaluated by standard MTT assay.