(S)-1-[2-(1,3-Dioxan-2-yl)phenyl]ethane-1,2-diol | 233253-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (S)-1-[2-(1,3-Dioxan-2-yl)phenyl]ethane-1,2-diol
• 英文别名: (S)-1-(2-(1,3-dioxan-2-yl)phenyl)ethan-1,2-diol；(1S)-1-[2-(1,3-dioxan-2-yl)phenyl]ethane-1,2-diol
• CAS: 233253-69-5
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: XVQGKKIKDMSXOY-LLVKDONJSA-N

物化性质

• 沸点：
  418.8±40.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (S)-1-[2-(1,3-Dioxan-2-yl)phenyl]ethane-1,2-diol 在 盐酸 、 sodium hydroxide 、 四氯化锡 、 三乙胺 作用下， 以 1,4-二氧六环 、 1,2-二氯乙烷 、 甲苯 为溶剂， 生成 1-((1R,3S)-3-Hydroxymethyl-1,3-dihydro-isobenzofuran-1-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  1,3-Dihydrobenzo[ c ]furan nucleoside analogues: additional studies of the thymine derivative

  摘要：

  The detailed study of the 1,3-dihydrobenzo[c]furan derivative of thymine is reported. The lack of anti-HIV activity of this compound in cell culture experiments is shown to be related to the inability of the corresponding 5'-triphosphate derivative to interact efficiently with the reverse transcriptase. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.031
• 作为产物：
  描述：

  邻苯二甲醛 在 AD-mix-α 、 potassium tert-butylate 、 对甲苯磺酸 作用下， 以 水 、 甲苯 、 叔丁醇 为溶剂， 生成 (S)-1-[2-(1,3-Dioxan-2-yl)phenyl]ethane-1,2-diol
  参考文献：
  名称：

  异苯并呋喃酮的（3S）和（3R）α，β-丁烯酰胺类似物的对映体过量测定，纯化和生物学评估。

  摘要：

  据报道，新的潜在抗病毒药物异苯并呋喃类似物的不对称合成。高效液相色谱（HPLC）是选择用于分离对映异构体的技术。我们描述这种手性分离，然后确定对映体过量。给出了每种测试对映体的生物学结果。

  DOI：

  10.1016/j.bmcl.2004.11.065

文献信息

• Stereoisomeric pyrimidine nucleoside analogues based on the 1,3-dihydrobenzo[c]furan core
  作者：David F. Ewing、Nour-Eddine Fahmi、Christophe Len、Grahame Mackenzie、Alessandra Pranzo

  DOI：10.1039/b006417n

  日期：——

  efficient route is described to uracil, thymidine and cytosine derivatives of 1,3-dihydrobenzo[c]furan which are aromatic analogues of the well known antiviral 2′,3′-dideoxy-2′,3′-didehydronucleosides. These systems contain two chiral centres (corresponding to α/β and D/L centres in a furanose sugar) and a route involving application of the Sharpless asymmetric oxidation methodology allowed access to

  一种新的有效途径被描述为 尿嘧啶， 胸苷 和胞嘧啶衍生物 1,3-二氢苯并[ c ]呋喃它们是众所周知的抗病毒2′，3′-二脱氧-2′，3′-二氢核苷的芳族类似物。这些系统包含两个手性中心（对应于呋喃糖中的α/β和D / L中心），并且涉及应用Sharpless不对称氧化方法的途径允许以对映体纯净形式接近尿嘧啶衍生物的四个立体异构体。
• Simple and Stereoselective Syntheses of Nucleoside Analogues with a Benzo[c]furan Glycone Moiety
  作者：David F. Ewing、Noureddine Fahmi、Grahame Mackenzie、Alessandra Pranzo

  DOI：10.1080/15257779908041494

  日期：1999.4

  A series of d4T analogues have been synthesised in which the 2',3'didehydro-2',3'-dideoxyribose moiety is replaced by a benzo[c]furan core. A simple strategy has been developed to access a range of compounds for biological screening. In addition, a stereoselective approach has been achieved with view to permit more detailed studies.
• Asymmetric synthesis of thymine nucleoside analogues based on the isochroman core
  作者：Christophe Len、Bruno Violeau

  DOI：10.1016/j.tetlet.2005.05.091

  日期：2005.7

  Diastereoisomeric analogues of d4T having an isochroman core as the glycone moiety have been prepared in seven steps. Starting from phthalaldehyde, two chiral centres analogous to the alpha/beta anomers of D/L sugars were created. The first was obtained enantiomerically pure via asymmetric dihydroxylation and the second via cyclisation of an aldehyde group with a primary hydroxyl group. Retention of chiral integrity at the C-4 Site enabled enantiomerically pure nucleoside analogues to be obtained. (c) 2005 Elsevier Ltd. All rights reserved.
• Enantiomeric d4T analogues and their structural determination
  作者：Abdelmajid Selouane、Claude Vaccher、Pierre Villa、Denis Postel、Christophe Len

  DOI：10.1016/s0957-4166(02)00106-4

  日期：2002.3

  Asymmetric synthesis of d4T analogues having a benzo[c]furan moiety with two asymmetric carbon atoms was realized using Sharpless asymmetric dihydroxylation as the key step in a synthesis starting from o-phthalaldehyde. Enantiomeric purities were determined by analytical chiral HPLC with an amylose-derived stationary phase, while the absolute configurations were established by X-ray crystallography. (C) 2002 Elsevier Science Ltd. All rights reserved.