Thioacetic acid S-((3aS,4S,7S,7aR)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl) ester | 592523-99-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Thioacetic acid S-((3aS,4S,7S,7aR)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl) ester
• CAS: 592523-99-4
• 化学式: C₁₁H₁₈O₅S
• 分子量: 262.327
• InChiKey: RQSVIVUKBRGOOW-XKNYDFJKSA-N

物化性质

• 沸点：
  346.6±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Thioacetic acid S-((3aS,4S,7S,7aR)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl) ester 在 三氟乙酸 、 硫酸 、 溶剂黄146 作用下， 反应 50.0h， 以58%的产率得到1,2,3,5-tetra-O-acetyl-4-thio-β-L-ribofuranose
  参考文献：
  名称：

  Synthesis and biological evaluation of some novel 4′-Thio-l-ribonucleosides with modified nucleobase moieties

  摘要：

  1,2,3,5-Tetra-O-acetyl-4-thio-beta-L-ribofuranose (13) was synthesized by an improved five-step sequence starting from methyl alpha-D-lyxopyranoside. Compound 13 was then converted to the corresponding L-4'-thionucleosides 4-6 and 19 by a modified Vorbruggen procedure. All of these nucleoside analogues were tested for their antitumour activity in vitro. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00289-0
• 作为产物：
  描述：

  methyl 2,3-O-isopropylidene-α-D-lyxopyranose 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 Thioacetic acid S-((3aS,4S,7S,7aR)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl) ester
  参考文献：
  名称：

  Synthesis and biological evaluation of some novel 4′-Thio-l-ribonucleosides with modified nucleobase moieties

  摘要：

  1,2,3,5-Tetra-O-acetyl-4-thio-beta-L-ribofuranose (13) was synthesized by an improved five-step sequence starting from methyl alpha-D-lyxopyranoside. Compound 13 was then converted to the corresponding L-4'-thionucleosides 4-6 and 19 by a modified Vorbruggen procedure. All of these nucleoside analogues were tested for their antitumour activity in vitro. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00289-0