[(2R,5S)-5-[(2S,5R)-5-(hydroxymethyl)oxolan-2-yl]oxolan-2-yl]methanol | 1236360-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: [(2R,5S)-5-[(2S,5R)-5-(hydroxymethyl)oxolan-2-yl]oxolan-2-yl]methanol
• CAS: 1236360-48-7
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: LBBCYPJJERZPOB-IMSYWVGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2R,5S)-5-[(2S,5R)-5-(hydroxymethyl)oxolan-2-yl]oxolan-2-yl]methanol 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Studies toward a Library of Tetrahydrofurans: Click and MCR Products of Mono- And Bis-Tetrahydrofurans

  摘要：

  Mono- and bis-tetrahydrofuran-based chemical libraries with diverse structural features have been prepared using the Sharpless azide-alkyne Click reaction and multi-component reactions (MCRs) such as Ugi and Biginelli reactions. Mono- and bis-tetrahydrofuran methyl azides, amines and ureas were key intermediates in these processes, and they were synthesized from the corresponding tetrahydrofuran methyl alcohols by mesylation followed by substitution with azide, reduction of the azide to the amine, and urea formation, as needed. Most mono- and tetrahydrofuran methyl alcohols were obtained by a Sharpless asymmetric dihydroxylation reaction. Alternatively, several mono-tetrahydrofurans were prepared by a cobalt(II) complex-catalyzed oxidative cyclization of bis-homoallylic alcohols, which were obtained by copper(I) iodide-catalyzed epoxide opening of 5,6-epoxyhex-1-ene with various alkyl and aryl Grignard reagents. These compounds are examples of an entirely new class of molecules in hitherto unknown chemical space, though their functions are yet to be determined presumably through random screening.

  DOI：

  10.1021/cc1000709
• 作为产物：
  描述：

  [(2R,5S,6S,9R)-1,2,9,10-tetrahydroxy-6-methylsulfonyloxydecan-5-yl] methanesulfonate 以 吡啶 为溶剂， 反应 4.0h， 生成 [(2R,5S)-5-[(2S,5R)-5-(hydroxymethyl)oxolan-2-yl]oxolan-2-yl]methanol
  参考文献：
  名称：

  Alteration of the Bis-tetrahydrofuran Core Stereochemistries in Asimicin Can Affect the Cytotoxicity

  摘要：

  A systematic analysis using 10 synthetic asimicin stereoisomers revealed that the stereochemistry of the bis-tetrahydrofuran core, including the tetrahydrofuran rings and the adjacent hydroxy functions, had significant effect on its cytotoxicity. Our findings set to rest the highly controversial perception that the stereochemistry of the tetrahydrofuran core has little effect on the activity, which is not true for its cytotoxic effect, and also reinforces the previous conclusion that asimicin is a highly potent anticancer compound.

  DOI：

  10.1021/jm801028c

文献信息

• Stereoselective Synthesis of <i>cis</i>-2,5-Disubstituted THFs: Application to Adjacent Bis-THF Cores of Annonaceous Acetogenins
  作者：Hiromichi Fujioka、Ryota Maehata、Shintaro Wakamatsu、Kenji Nakahara、Tatsuya Hayashi、Tomohiro Oki

  DOI：10.1021/ol203425p

  日期：2012.2.17

  intermediates. N-Iodosuccinimide (NIS) effectively worked as an activator of the double bonds in the substrates and the silyl enol ether. Application to an expedient synthesis of the adjacent bis-tetrahydrofuran core of Annonaceous acetogenins with a cis/threo/cis relative stereochemistry is also described.

  在甲硅烷基烯醇醚的存在下，γ，δ-不饱和醇的碘环化通过甲硅烷氧基中间体在一个罐中产生了顺式-2,5-二取代的四氢呋喃。N-碘代琥珀酰亚胺（NIS）有效地用作底物和甲硅烷基烯醇醚中双键的活化剂。还描述了用于具有顺/苏/顺/顺相对立体化学的壬基产乙酸原的相邻双-四氢呋喃核的合成的应用。
• Alteration of the Bis-tetrahydrofuran Core Stereochemistries in Asimicin Can Affect the Cytotoxicity
  作者：Subhash C. Sinha、Zhiyong Chen、Zheng-Zheng Huang、Eiko Nakamaru-Ogiso、Halina Pietraszkiewicz、Matthew Edelstein、Frederick Valeriote

  DOI：10.1021/jm801028c

  日期：2008.11.27

  A systematic analysis using 10 synthetic asimicin stereoisomers revealed that the stereochemistry of the bis-tetrahydrofuran core, including the tetrahydrofuran rings and the adjacent hydroxy functions, had significant effect on its cytotoxicity. Our findings set to rest the highly controversial perception that the stereochemistry of the tetrahydrofuran core has little effect on the activity, which is not true for its cytotoxic effect, and also reinforces the previous conclusion that asimicin is a highly potent anticancer compound.
• Studies toward a Library of Tetrahydrofurans: Click and MCR Products of Mono- And Bis-Tetrahydrofurans
  作者：Jitendra K. Mishra、Peter Wipf、Subhash C. Sinha

  DOI：10.1021/cc1000709

  日期：2010.9.13

  Mono- and bis-tetrahydrofuran-based chemical libraries with diverse structural features have been prepared using the Sharpless azide-alkyne Click reaction and multi-component reactions (MCRs) such as Ugi and Biginelli reactions. Mono- and bis-tetrahydrofuran methyl azides, amines and ureas were key intermediates in these processes, and they were synthesized from the corresponding tetrahydrofuran methyl alcohols by mesylation followed by substitution with azide, reduction of the azide to the amine, and urea formation, as needed. Most mono- and tetrahydrofuran methyl alcohols were obtained by a Sharpless asymmetric dihydroxylation reaction. Alternatively, several mono-tetrahydrofurans were prepared by a cobalt(II) complex-catalyzed oxidative cyclization of bis-homoallylic alcohols, which were obtained by copper(I) iodide-catalyzed epoxide opening of 5,6-epoxyhex-1-ene with various alkyl and aryl Grignard reagents. These compounds are examples of an entirely new class of molecules in hitherto unknown chemical space, though their functions are yet to be determined presumably through random screening.