(3R,4S,5R)-2,3,4,5-tetramethoxytetrahydro-2H-pyran | 20188-52-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5R)-2,3,4,5-tetramethoxytetrahydro-2H-pyran
• 英文别名: methyl 2,3,4-tri-O-methyl-D-xylopyranoside；(3R,4S,5R)-2,3,4,5-tetramethoxyoxane
• CAS: 20188-52-7
• 化学式: C₉H₁₈O₅
• 分子量: 206.239
• InChiKey: OQFUMNZJTHPYPI-OBCZXFEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-2,3,4,5-tetramethoxytetrahydro-2H-pyran 在 三氟甲磺酸 、 三氟甲磺酸三甲基硅酯 、 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 1.0h， 生成 (+)-α,α-clavosolide A
  参考文献：
  名称：

  海洋天然产物（-）-clavosolide A的全合成。Petasis-Ferrier联合/重组策略的展示。

  摘要：

  [结构：见正文]利用Petasis-Ferrier结合/重排策略构建必要的糖苷配基单体，从市售巴豆醛以17个步骤（最长的线性序列）完成了海洋乙交酯（-）-clavosolide A的总合成。使用Yamaguchi方案进行一锅酯化/内酯化，然后进行双糖苷化，提供（-）-clavosolideA。

  DOI：

  10.1021/ol0611752
• 作为产物：
  描述：

  (2S,3R,4S,5R)-2-[(2S,3R,4R,5R,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxyoxane-3,4,5-triol 生成 (3R,4S,5R)-2,3,4,5-tetramethoxytetrahydro-2H-pyran
  参考文献：
  名称：

  NAKANO, KIMIKO;MATSUDA, EMI;TSURUMI, KAORI;YAMASAKI, TOKUSHI;MURAKAMI, KO+, PHYTOCHEMISTRY, 27,(1988) N 10, C. 3235-3239

  摘要：

  DOI：

文献信息

• Enantioselective Total Synthesis of (-)-Clavosolide A and B
  作者：Jung-Beom Son、Si-Nae Kim、Na-Yeong Kim、Min-Ho Hwang、Won-Sun Lee、Duck-Hyung Lee

  DOI：10.5012/bkcs.2010.31.03.653

  日期：2010.3.20

  Enantioselective total synthesis of (-)-clavosolide A and B was reported in full including the synthesis of proposed structure of (-)-clavosoldie A (1), revised structure of (-)-clavosoldie A (5), and revised structure of (-)-clavosoldie B (6). The relative and absolute stereochemistries of the natural products were confirmed unambiguously by comparing the optical rotation values and $^1H$ and $^13}C$ NMR spectra of them.

  完全报道了(-)-clavosolide A和B的对映选择性全合成，包括所提出的(-)-clavosolide A (1)结构的合成、修订后的(-)-clavosolide A (5)结构的合成以及修订后的(-)-clavosolide B (6)结构的合成。通过比较其旋光值和$^1H$及$^13}C$核磁共振谱，明确证实了这些天然产物的相对和绝对立体化学。
• Conformational studies of glycosylated cyclic oligomers of furanoid sugar amino acids
  作者：Nishant Singh、Pancham Singh Kandiyal、Praveen Kumar Shukla、Ravi Sankar Ampapathi、Tushar Kanti Chakraborty

  DOI：10.1016/j.tet.2016.07.071

  日期：2016.9

  library of sugar amino acids (SAA). Conformational analyses carried out by NMR suggested that these cyclic dimers and trimers have well-defined structures in solution. MD simulations performed based on the restraints obtained from NMR revealed that C2H and CO are positioned outside the plane of the ring and NHs are pointed inside the ring. It was encouraging to note that while the cyclic non-glycosylated

  分子的糖基化改善了它们的药理和药代动力学特性。在当前的手稿中，我们探讨了糖基化对构型明确的小环均聚物的结构和功能的影响，该结构衍生自糖氨基酸（SAA）结构上不同的文库。通过NMR进行的构象分析表明，这些环状二聚体和三聚体在溶液中具有明确的结构。基于从NMR获得的约束条件进行的MD模拟显示，C2H和CO位于环平面之外，而NHs则指向环内部。令人鼓舞的是，尽管环状非糖基化的均聚物根本不显示任何抗菌活性，但它们的糖基化对应物却显示出相对更好的活性。
• Total Synthesis of Clavosolide A via Asymmetric Alcohol‐Mediated Carbonyl Allylation: Beyond Protecting Groups or Chiral Auxiliaries in Polyketide Construction
  作者：James M. Cabrera、Michael J. Krische

  DOI：10.1002/anie.201906259

  日期：2019.7.29

  The 20‐membered marine macrodiolide clavosolide A is prepared in 7 steps (LLS) in the absence of protecting groups or chiral auxiliaries via enantioselective alcohol‐mediated carbonyl addition. In 9 prior total syntheses, 11–34 steps (LLS) were required.

  20 元海洋大二内酯 clavosolide A 在没有保护基团或手性助剂的情况下，通过对映选择性醇介导的羰基加成，经过 7 个步骤 (LLS) 制备。在之前的 9 次全合成中，需要 11-34 个步骤 (LLS)。
• MESOGENIC COMPOUND, LIQUID-CRYSTAL MEDIUM AND LIQUID CRYSTAL DISPLAY
  申请人：MERCK PATENT GMBH

  公开号：US20160115388A1

  公开（公告）日：2016-04-28

  The instant invention relates to mesogenic compounds of formula I-Z to mesogenic media, preferably exhibiting a blue phase, comprising a component, component A, consisting of one or more compounds of formula I-Z, and, preferably, a second component, component B, consisting of one or more compounds selected from the group of compounds of formulae I-M and I-U, wherein the parameters are as specified in the text, preferably stabilised by a polymer, and their use in electro-optical light modulation elements and their respective use in displays, as well as to such displays.

  本发明涉及公式I-Z的介向化合物，用于介向介质，优选是表现为蓝相的介向介质，包括一个组分A，由一个或多个公式I-Z的化合物组成，以及优选的第二组分B，由从公式I-M和I-U的化合物组中选择的一个或多个化合物组成，其中参数如文本所述，优选由聚合物稳定，并且它们在电光调制元件中的使用及其在显示器中的相应使用，以及这样的显示器。
• Total Synthesis, Structural Revision, and Absolute Configuration of (+)-Clavosolide A
  作者：Jung Beom Son、Si Nae Kim、Na Yeong Kim、Duck Hyung Lee

  DOI：10.1021/ol052851n

  日期：2006.2.1

  Enantioselective synthesis of 3, a revised structure for clavosolide A, was completed. Both H-1 and C-13 NMR spectra of the natural and synthetic compounds were identical, and optical rotation measurements identified the absolute configuration of the natural clavosolide A as the enantiomer of 3.