Trifluoro-methanesulfonic acid (3aS,4S,7R,7aR)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester | 592523-98-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Trifluoro-methanesulfonic acid (3aS,4S,7R,7aR)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester
• 英文别名: [(3aS,4S,7R,7aR)-4-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] trifluoromethanesulfonate
• CAS: 592523-98-3
• 化学式: C₁₀H₁₅F₃O₇S
• 分子量: 336.286
• InChiKey: AUUZJBOAISBXFR-KVPKETBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (3aS,4S,7R,7aR)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 、 potassium thioacetate 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 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
• 作为产物：
  描述：

  methyl α-D-lyxopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 24.5h， 生成 Trifluoro-methanesulfonic acid (3aS,4S,7R,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

文献信息

• Synthesis and biological evaluation of some novel 4′-Thio-l-ribonucleosides with modified nucleobase moieties
  作者：Vjera Pejanović、Zdenka Stokić、Biljana Stojanović、Vesna Piperski、Mirjana Popsavin、Velimir Popsavin

  DOI：10.1016/s0960-894x(03)00289-0

  日期：2003.6

  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.