(1S,2R)-2-(hydroxymethyl)cyclopent-3-enol | 850224-36-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R)-2-(hydroxymethyl)cyclopent-3-enol
• 英文别名: (1S,2R)-2-(hydroxymethyl)cyclopent-3-en-1-ol
• CAS: 850224-36-1
• 化学式: C₆H₁₀O₂
• 分子量: 114.144
• InChiKey: QMUPMIDPQMYBCF-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-(hydroxymethyl)cyclopent-3-enol 在 吡啶 、 4-二甲氨基吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,2R,3S,5R)-2-Trityloxymethyl-6-oxa-bicyclo[3.1.0]hexan-3-ol
  参考文献：
  名称：

  Isomers of neplanocin A and 2′-deoxyneplanocin A possessing a C-1′/C-6′ double bond

  摘要：

  Missing among the unsaturated carbocyclic nucleosides is the 1',6'-double bond isomer of neplanocin A. A practical synthesis of this compound and its 2'-deoxy derivative is reported from readily accessible cyclopentenols. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.061
• 作为产物：
  描述：

  (1S,4R)-顺式-4-乙酰氧基-2-环戊烯-1-醇 在 potassium fluoride 、 双氧水 、 potassium hydrogencarbonate 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二溴乙烷 为溶剂， 反应 35.16h， 生成 (1S,2R)-2-(hydroxymethyl)cyclopent-3-enol
  参考文献：
  名称：

  Synthesis and biological evaluation of phosphoramidate prodrugs of two analogues of 2-deoxy-d-ribose-1-phosphate directed to the discovery of two carbasugars as new potential anti-HIV leads

  摘要：

  2-Deoxy-alpha-D-ribose-1-phosphate is of great interest as it is involved in the biosynthesis and/or catabolic degradation of several nucleoside analogues of biological and therapeutic relevance. However due to the lack of a stabilising group at its 2-position, it is difficult to synthesize stable prodrugs of this compound. In order to overcome this lack of stability, the synthesis of carbasugar analogues of 2-deoxyribose-1-phosphate was envisioned. Herein the preparation of a series of prodrugs of two carbocyclic analogues of 2-deoxyribose-1-phosphate using the phosphoramidate ProTide technology, along with their biological evaluation against HIV and cancer cell proliferation, is reported. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.039

文献信息

• Synthesis and Analysis of Oligonucleotides Containing Abasic Site Analogues
  作者：Haidong Huang、Marc M. Greenberg

  DOI：10.1021/jo702614p

  日期：2008.4.1

  to selectively incorporate nucleotides opposite them. However, it was not possible to determine the structural basis for this molecular recognition from these experiments. A group of oligonucleotides containing analogues of the AP and L lesions were synthesized and characterized as probes to gain insight into the structural basis for the distinct effect of 2-deoxyribonolactone on replication. These molecules

  DNA 损伤导致糖苷键 (AP) 的正式水解和几个氧化的脱碱基损伤形成脱碱基位点。先前对 AP 位点的研究表明，在大肠杆菌中约80% 的复制事件中，DNA 聚合酶优先掺入与它们相对的 dA. 这些结果与 AP 位点是无指导性病变的假设一致，因为没有 Watson-Crick 碱基，其旁路遵循“A 规则”。最近对氧化脱碱基损伤 2-脱氧核糖内酯 (L) 的复制研究表明，DNA 聚合酶在绕过它时不应用 A 规则并结合大量与 L 相对的 dG。这些研究表明脱碱基位点，例如L 确实引导聚合酶选择性地掺入与其相对的核苷酸。然而，无法从这些实验中确定这种分子识别的结构基础。合成了一组包含 AP 和 L 病变类似物的寡核苷酸，并将其表征为探针，以深入了解 2-脱氧核糖内酯对复制的独特影响的结构基础。