(1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-ol | 681853-93-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-ol
• 英文别名: (-)-(R)-1-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldiphenylsilyloxy)ethanol；(R)-2-((tert-butyldiphenylsilyl)oxy)-1-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethanol；(R)-2-[(tert-butyldiphenylsilyl)oxy]-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]ethan-1-ol；(1R,4R,5S)-(-)-2-(tert-butyldiphenylsilyloxy)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-ethan-1-ol；1,2-dideoxy-6-O-(tert-butyldiphenylsilyloxy)-3,4-di-O-isopropylidene-D-ribo-hex-1-enitol；(R)-2-(tert-butyldiphenylsilyloxy)-1-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethanol；(1R)-2-[tert-butyl(diphenyl)silyl]oxy-1-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol
• CAS: 681853-93-0
• 化学式: C₂₅H₃₄O₄Si
• 分子量: 426.628
• InChiKey: NDLIDUKXIFASES-XPWALMASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-ol 在 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (R)-2-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(methoxymethoxy)ethanol
  参考文献：
  名称：

  Divergent synthesis of various iminocyclitols from d-ribose

  摘要：

  报道了一种从核糖醛衍生物开始，高度选择性地合成多羟基吡咯烷、哌啶和氮杂环庚烷的有效路线。

  DOI：

  10.1039/c5ob01042j
• 作为产物：
  描述：

  2,3-O-isopropylidene-D-ribose 在 咪唑 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.83h， 生成 (1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-ol
  参考文献：
  名称：

  First total synthesis and structure confirmation of diacetylenic polyol (+)-oploxyne B

  摘要：

  The first total synthesis of the natural product (+)-oploxyne B is achieved. The synthesis has led to the confirmation of absolute stereochemistry of the natural product. The natural product displayed cytotoxic activity with IC50 values varying from 16 to 53 mu M in four cancer cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.020

文献信息

• [EN] COMPOUNDS AND METHODS FOR TREATING ADDICTION AND RELATED DISORDERS<br/>[FR] COMPOSÉS ET MÉTHODES DE TRAITEMENT D'UNE DÉPENDANCE ET DE TROUBLES ASSOCIÉS
  申请人：ASTROCYTE PHARMACEUTICALS INC

  公开号：WO2019157317A1

  公开（公告）日：2019-08-15

  The present invention relates to compounds and methods of use thereof for treatment of certain disorders and conditions, for example an addiction or compulsive disorder.

  本发明涉及化合物及其治疗某些疾病和症状的方法，例如成瘾或强迫性障碍。
• Total Syntheses of a Conformationally Locked<i>North</i>-Type Methanocarba Puromycin Analogue and a Dinucleotide Derivative
  作者：Benoît Y. Michel、Peter Strazewski

  DOI：10.1002/chem.200802629

  日期：2009.6.15

  Locked in translation: Crucial insight into the ribosomal catalysis of peptide‐bond formation is expected to be gained from the target compounds, which feature conformational locking in a North‐type pucker, designed to interfere with the translation of the genetic code. The compounds were prepared from D‐ribose in 18 and 19 steps by a multi‐step synthetic route described here (see scheme).

  锁定翻译：可以从目标化合物中获得对肽键形成的核糖体催化作用的重要见解，这些化合物具有构象锁定在North- type pucker中的功能，旨在干扰遗传密码的翻译。这些化合物是由D-核糖按照此处所述的多步合成路线分18步和19步制备的（请参见方案）。
• Synthesis, activity and metabolic stability of non-ribose containing inhibitors of histone methyltransferase DOT1L
  作者：Lisheng Deng、Li Zhang、Yuan Yao、Cong Wang、Michele S. Redell、Shuo Dong、Yongcheng Song

  DOI：10.1039/c3md00021d

  日期：——

  Histone methyltransferase DOT1L is a drug target for MLL leukemia. We report an efficient synthesis of a cyclopentane-containing compound that potently and selectively inhibits DOT1L (Ki = 1.1 nM) as well as H3K79 methylation (IC50 ∼ 200 nM). Importantly, this compound exhibits a high stability in plasma and liver microsomes, suggesting it is a better drug candidate.

  组蛋白甲基转移酶 DOT1L 是 MLL 白血病的药物靶点。我们报告了一种含环戊烷化合物的有效合成，该化合物有效且选择性地抑制 DOT1L ( K i = 1.1 nM) 以及 H3K79 甲基化 (IC 50 ∼ 200 nM)。重要的是，该化合物在血浆和肝微粒体中表现出高稳定性，表明它是更好的候选药物。
• A Further Contribution to the Study of Sagittamide A: Synthesis of a Pivotal Intermediate Belonging to a Rare L-Series
  作者：Anne Humbert、Karen Plé、Dominique Harakat、Agathe Martinez、Arnaud Haudrechy

  DOI：10.3390/molecules17077709

  日期：——

  A key saggitamide intermediate corresponding to a rare sugar framework has been obtained. This approach should help to establish the overall configuration of more complex structures of the sagittamide family.

  我们获得了一种与稀有糖框架相对应的关键箭毒酰胺中间体。这种方法有助于确定箭头酰胺家族更复杂结构的整体构型。
• Development of Bicyclo[3.1.0]hexane-Based A3 Receptor Ligands: Closing the Gaps in the Structure–Affinity Relationships
  作者：Jan Phillip Lemmerhirt、Andreas Isaak、Rongfang Liu、Max Kock、Constantin G. Daniliuc、Kenneth A. Jacobson、Laura H. Heitman、Anna Junker

  DOI：10.3390/molecules27072283

  日期：——

  inflammation and cancer. In this paper, a series of bicyclo[3.1.0]hexane-based nucleosides was synthesized and evaluated for their P1 receptor affinities in radioligand binding studies. The study focused on modifications at 1-, 2-, and 6-positions of the purine ring and variations of the 5′-position at the bicyclo[3.1.0]hexane moiety, closing existing gaps in the structure–affinity relationships. The most

  腺苷A 3受体是治疗和诊断炎症和癌症的有希望的靶标。在本文中，合成了一系列基于双环[3.1.0]己烷的核苷，并在放射性配体结合研究中评估了它们对 P1 受体的亲和力。该研究的重点是嘌呤环的 1-、2-和 6-位修饰以及双环[3.1.0]己烷部分 5'-位的变化，以弥补结构-亲和力关系中现有的空白。最有效的衍生物30显示出中等的 A 3 AR 亲和力（K i为 0.38 μM）和高 A 3 R 选择性。在功能性 P2Y 1中进一步评估了在 5'-位置变化的化合物子集R 分析，显示没有脱靶活性。