(3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-ol | 14187-51-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-ol
• 英文别名: (3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydropyran-2-ol；2,3,4-tri-O-methyl-α-L-rhamnopyranose；2,3,4-tri-O-methyl-L-rhamnose；2,3,4-tri-O-methy-L-rhamnose；2,3,4-tri-O-methylrhamnose；(3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-ol；(3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyloxan-2-ol
• CAS: 14187-51-0
• 化学式: C₉H₁₈O₅
• 分子量: 206.239
• InChiKey: VNYQTDHNVPPMHV-WMOCKQOXSA-N

物化性质

• 沸点：
  280.4±40.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-ol 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 3',4'-di-O-methylaranciamycin
  参考文献：
  名称：

  Inhibition of collagenase by aranciamycin and aranciamycin derivatives.

  摘要：

  Aranciamycin (1), an anthracycline antibiotic, was found to be an inhibitor of Clostridium histolyticum collagenase, with an IC50 = 3.7 x 10(-7) M. Elastase and trypsin were not inhibited at concentrations less-than-or-equal-to 10(-5) M. A number of aranciamycin derivatives 2-13 were prepared and tested for collagenase inhibition. While loss of activity was found for derivatives modified in the sugar ring or rings B and D of the aglycone, increased potency was found when the tertiary alcohol at C-9 was esterified. All compounds 1-13 were found to inhibit DNA synthesis of Yoshida sarcoma tumor cells.

  DOI：

  10.1021/jm00093a008
• 作为产物：
  描述：

  芦丁 生成 (3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-ol
  参考文献：
  名称：

  KHATOON, FEHMEEDA;KHABIRUDDIN, MD.;ASIF, M.;ANSARI, W. H., J. INDIAN CHEM. SOC., 66,(1989) N, C. 287-288

  摘要：

  DOI：

文献信息

• PESTICIDAL COMPOSITIONS
  申请人：Crouse Gary D.

  公开号：US20090209476A1

  公开（公告）日：2009-08-20

  The invention disclosed in this document is related to the field of pesticides and their use in controlling pests. A compound having the following structure is disclosed.

  这份文件中披露的发明涉及杀虫剂领域及其在控制害虫方面的应用。披露了一种具有以下结构的化合物。
• [EN] PESTICIDAL COMPOUNDS<br/>[FR] COMPOSÉS PESTICIDES
  申请人：BASF SE

  公开号：WO2018177781A1

  公开（公告）日：2018-10-04

  The present invention relates to the compounds of formula (I), and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof wherein the variables are defined according to the description, (I). The compounds of formula (I), as well as the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof, are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

  本发明涉及式(I)的化合物，以及其N-氧化物、立体异构体、互变异构体和农业或兽医可接受的盐，其中变量根据描述(I)中定义。式(I)的化合物以及其N-氧化物、立体异构体、互变异构体和农业或兽医可接受的盐对于对抗或控制无脊椎动物害虫，特别是节肢动物害虫和线虫是有用的。该发明还涉及一种通过使用这些化合物来控制无脊椎动物害虫的方法，以及包括所述化合物的植物繁殖材料和农业和兽医组合物。
• Synthesis of Novel Spinosyn A Analogues by Pd-Mediated Transformations
  作者：Lutz F. Tietze、Gordon Brasche、Alexander Grube、Niels Böhnke、Christian Stadler

  DOI：10.1002/chem.200700464

  日期：2007.10.15

  new or modified established pesticides to avoid the development of serious resistances. Recent reports on the insecticidal spinosyns 1 and 2 show that also this class of pest managing agents is increasingly exposed to the formation of resistances. The synthesis of new derivatives is therefore highly desirable. We describe in this paper a convergent approach towards novel enantiopure spinosyn A analogues

  现代作物保护的概念要求不断供应新的或改良的既定农药，以避免产生严重的抗药性。关于杀虫多杀菌素1和2的最新报道表明，这类害虫处理剂也日益暴露于抗药性的形成。因此，非常需要合成新的衍生物。我们在本文中描述了一种对类型3的新型对映纯多杀菌素A类似物的收敛方法，该方法基于对结构-活性关系的研究，并采用了双重Heck反应作为制备三环骨架组装的关键步骤。
• Studies on Catalytic Enantioselective Total Synthesis of Caprazamycin B: Construction of the Western Zone
  作者：Purushothaman Gopinath、Takumi Watanabe、Masakatsu Shibasaki

  DOI：10.1021/jo301803h

  日期：2012.10.19

  catalyst furnished the β-hydroxy thioamide in good yield and enantioselectivity. On further transformation, the thioamide functionality was converted to the corresponding β-hydroxy ester. Finally, a convergent synthesis of the western zone of caprazamycin B was achieved by connecting the hemiester, the β-hydroxy ester, and the 2,3,4-tri-O-methyl-l-rhamnose fragments.

  我们描述了使用两个催化不对称反应作为我们方法的关键要素的一种简单便捷的卡普沙霉素B西部区域的合成方法。以（S）-Ni 2-（席夫碱）络合物为催化剂对3-甲基戊二酸酐进行不对称化反应，得到了手性半酯，以及与间苯二酚，（R，R）-Ph-BPE和2的硫酰胺-醛醇缩合反应， 2,5,7,8-五甲基苯并二氢苯并二氢苯并二氢吡喃醇作为催化剂以良好的产率和对映选择性提供了β-羟基硫代酰胺。进一步转化后，将硫酰胺官能团转化为相应的β-羟基酯。最后，通过连接半酯，β-羟基酯和2,3,4-tri-O-甲基-1-鼠李糖片段。
• Total Synthesis of Caprazamycin A: Practical and Scalable Synthesis of <i>syn</i>-β-Hydroxyamino Acids and Introduction of a Fatty Acid Side Chain to 1,4-Diazepanone
  作者：Hugh Nakamura、Chihiro Tsukano、Takuma Yoshida、Motohiro Yasui、Shinsuke Yokouchi、Yusuke Kobayashi、Masayuki Igarashi、Yoshiji Takemoto

  DOI：10.1021/jacs.9b02220

  日期：2019.5.29

  Diastereoselective aldol reactions of aldehydes 12 and 25-27, derived from uridine, with diethyl isocyanomalonate 13 and phenylcarbamate 21 were investigated using thiourea catalysts 14 or bases to synthesize syn-β-hydroxyamino acid derivatives. The 1,4-diazepanone core of 1 was constructed using a Mitsunobu reaction, and the fatty acid side chain was introduced using a stepwise sequence based on model studies.

  描述了具有代表性的脂核苷类抗生素 caprazamycin A (1) 的首次全合成。使用硫脲催化剂 14 或碱研究衍生自尿苷的醛 12 和 25-27 与异氰基丙二酸二乙酯 13 和氨基甲酸苯酯 21 的非对映选择性羟醛反应，以合成合成 β-羟基氨基酸衍生物。1 的 1,4-二氮杂环酮核心使用光信反应构建，并使用基于模型研究的逐步序列引入脂肪酸侧链。值得注意的是，使用钯黑和甲酸实现了整体脱保护，而无需氢化尿苷单元中的烯烃。