[2-(3,4,5-Trimethoxyphenyl)-1,3-dithian-2-yl]methanol | 828921-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [2-(3,4,5-Trimethoxyphenyl)-1,3-dithian-2-yl]methanol
• 英文别名: [2-(3,4,5-trimethoxyphenyl)-1,3-dithian-2-yl]methanol
• CAS: 828921-09-1
• 化学式: C₁₄H₂₀O₄S₂
• 分子量: 316.442
• InChiKey: DGKFSOPQRWRZGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  98.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [2-(3,4,5-Trimethoxyphenyl)-1,3-dithian-2-yl]methanol 在 吡啶 、 4-二甲氨基吡啶 、 1,4-环己二烯 、 (1-azabenzotriazole-1-yloxy)tripyrrolidinophosphonium*BF₆ 、 TEA 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 29.5h， 生成 Carbonic acid (3R,5S)-1-acetyl-5-phenethylcarbamoyl-pyrrolidin-3-yl ester 2-(3,4,5-trimethoxy-phenyl)-[1,3]dithian-2-ylmethyl ester
  参考文献：
  名称：

  Light-Directed Radial Combinatorial Chemistry:  Orthogonal Safety-Catch Protecting Groups for the Synthesis of Small Molecule Microarrays

  摘要：

  We describe the development of photolabile protecting groups based on the 3,4,5-trimethoxyphenacyl group (TMP). Orthogonal safety-catches were created by introducing an acid-activatible dimethyl ketal (AA-TMP) and an oxidatively activatible 1,3-dithiane (OA-TMP) into the photolabile TMP group. We demonstrate the application of these protecting groups in light-directed synthesis of small molecule microarrays with diversity elements radially attached to a hydroxyproline scaffold.

  DOI：

  10.1021/ja044702q
• 作为产物：
  描述：

  聚合甲醛 、 2-(3,4,5-trimethoxyphenyl)-1,3-dithiane 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 以58%的产率得到[2-(3,4,5-Trimethoxyphenyl)-1,3-dithian-2-yl]methanol
  参考文献：
  名称：

  Light-Directed Radial Combinatorial Chemistry:  Orthogonal Safety-Catch Protecting Groups for the Synthesis of Small Molecule Microarrays

  摘要：

  We describe the development of photolabile protecting groups based on the 3,4,5-trimethoxyphenacyl group (TMP). Orthogonal safety-catches were created by introducing an acid-activatible dimethyl ketal (AA-TMP) and an oxidatively activatible 1,3-dithiane (OA-TMP) into the photolabile TMP group. We demonstrate the application of these protecting groups in light-directed synthesis of small molecule microarrays with diversity elements radially attached to a hydroxyproline scaffold.

  DOI：

  10.1021/ja044702q

文献信息

• Method and system for the generation of large double stranded DNA fragments
  申请人：Cerrina Francesco

  公开号：US20070196834A1

  公开（公告）日：2007-08-23

  Synthesis of long chain molecules such as DNA is carried out rapidly and efficiently to produce relatively large quantities of the desired product. The synthesis of an entire gene or multiple genes formed of many hundreds or thousands of base pairs can be accomplished rapidly and, if desired, in a fully automated process requiring minimal operator intervention, and in a matter of hours, a day or a few days rather than many days or weeks. Production of a desired gene or set of genes having a specified base pair sequence is initiated by analyzing the specified target sequence and determining an optimal set of subsequences of base pairs that can be assembled to form the desired final target sequence. The set of oligonucleotides are then synthesized utilizing automated oligonucleotide synthesis techniques. The synthesized oligonucleotides are subsequently selectively released from the substrate and used in a sequential assembly process.
• Light-Directed Radial Combinatorial Chemistry:  Orthogonal Safety-Catch Protecting Groups for the Synthesis of Small Molecule Microarrays
  作者：Alex Shaginian、Madhusudan Patel、Mo-Huang Li、Shane T. Flickinger、Changhan Kim、Franco Cerrina、Peter J. Belshaw

  DOI：10.1021/ja044702q

  日期：2004.12.1

  We describe the development of photolabile protecting groups based on the 3,4,5-trimethoxyphenacyl group (TMP). Orthogonal safety-catches were created by introducing an acid-activatible dimethyl ketal (AA-TMP) and an oxidatively activatible 1,3-dithiane (OA-TMP) into the photolabile TMP group. We demonstrate the application of these protecting groups in light-directed synthesis of small molecule microarrays with diversity elements radially attached to a hydroxyproline scaffold.