4-(methoxymethylthio)butan-1-ol | 1206537-46-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 4-(methoxymethylthio)butan-1-ol
• 英文别名: 4-(Methoxymethylsulfanyl)butan-1-ol；4-(methoxymethylsulfanyl)butan-1-ol
• CAS: 1206537-46-3
• 化学式: C₆H₁₄O₂S
• 分子量: 150.242
• InChiKey: HYKZKWNXZQQHIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(methoxymethylthio)butan-1-ol 、 5‘-O-dimethoxytrityl-2’-deoxyribothymidine 3‘-O-phosphorodiamidite 在 四氮唑 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-3'-O-(4-methoxymethylthiobutoxy)-(N,N-diisopropylamino)phosphinyl-2'-deoxythymidine
  参考文献：
  名称：

  Assessment of heat-sensitive thiophosphate protecting groups in the development of thermolytic DNA oligonucleotide prodrugs

  摘要：

  Heat-sensitive thiophosphate protecting groups derived from the alcohol 4 or 10 have provided insights in the design of DNA oligonucleotide prodrugs. Indeed, functional groups stemming from the alcohol 9, 15, 16 or 22 may be applicable to thiophosphate protection of immunostimulatory CpG DNA motifs, whereas those originating from the alcohol 3, 5,12,13,18, 20 or 22 offer adequate protection of terminal phosphodiester functions against ubiquitous exonucleases that may be found in biological environments. Functional groups derived from the alcohol 9, 15, 16, 19 or 23 are suitable for the protection of phosphodiester functions flanking the CpG motifs of immunomodulatory DNA sequences. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2009.10.096
• 作为产物：
  描述：

  4-巯基-1-丁醇 、 氯甲基甲基醚 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 16.75h， 以29%的产率得到4-(methoxymethylthio)butan-1-ol
  参考文献：
  名称：

  Assessment of heat-sensitive thiophosphate protecting groups in the development of thermolytic DNA oligonucleotide prodrugs

  摘要：

  Heat-sensitive thiophosphate protecting groups derived from the alcohol 4 or 10 have provided insights in the design of DNA oligonucleotide prodrugs. Indeed, functional groups stemming from the alcohol 9, 15, 16 or 22 may be applicable to thiophosphate protection of immunostimulatory CpG DNA motifs, whereas those originating from the alcohol 3, 5,12,13,18, 20 or 22 offer adequate protection of terminal phosphodiester functions against ubiquitous exonucleases that may be found in biological environments. Functional groups derived from the alcohol 9, 15, 16, 19 or 23 are suitable for the protection of phosphodiester functions flanking the CpG motifs of immunomodulatory DNA sequences. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2009.10.096

文献信息

• Assessment of heat-sensitive thiophosphate protecting groups in the development of thermolytic DNA oligonucleotide prodrugs
  作者：Cristina Ausín、Jon S. Kauffman、Robert J. Duff、Shankaramma Shivaprasad、Serge L. Beaucage

  DOI：10.1016/j.tet.2009.10.096

  日期：2010.1

  Heat-sensitive thiophosphate protecting groups derived from the alcohol 4 or 10 have provided insights in the design of DNA oligonucleotide prodrugs. Indeed, functional groups stemming from the alcohol 9, 15, 16 or 22 may be applicable to thiophosphate protection of immunostimulatory CpG DNA motifs, whereas those originating from the alcohol 3, 5,12,13,18, 20 or 22 offer adequate protection of terminal phosphodiester functions against ubiquitous exonucleases that may be found in biological environments. Functional groups derived from the alcohol 9, 15, 16, 19 or 23 are suitable for the protection of phosphodiester functions flanking the CpG motifs of immunomodulatory DNA sequences. Published by Elsevier Ltd.