Trifluoro-methanesulfonic acid (R)-1-{(4S,5S)-5-[(2R,3R,4S)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-oxo-tetrahydro-furan-2-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester | 194918-23-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Trifluoro-methanesulfonic acid (R)-1-{(4S,5S)-5-[(2R,3R,4S)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-oxo-tetrahydro-furan-2-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester
• CAS: 194918-23-5
• 化学式: C₃₀H₅₉F₃O₁₀SSi₃
• 分子量: 753.11
• InChiKey: KVOTTXFTFIGMOS-YWIRWFRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  115.82
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (R)-1-{(4S,5S)-5-[(2R,3R,4S)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-oxo-tetrahydro-furan-2-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester 在 锂硼氢 、 sodium azide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1R,2R,3R)-1-{(4R,5R)-5-[(S)-1-Azido-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-butane-1,4-diol
  参考文献：
  名称：

  Synthesis of casuarines [pentahydroxylated pyrrolizidines] by sodium hydrogen telluride-induced cyclisations of azidodimesylates

  摘要：

  The key step in the synthesis of four diastereomers of casuarine from eight carbon sugar lactones is the efficient reduction of open chain azidodimesylates by sodium hydrogen telluride [Suzuki-Takaoka reduction] to allow the formation of the pyrrolizidine nucleus by bicyclisation. This is the first report of the synthesis of such highly oxygenated pyrrolizidines. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01306-3
• 作为产物：
  描述：

  三氟甲磺酸酐 、 (3S,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-{(4S,5R)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-dihydro-furan-2-one 以 二氯甲烷 为溶剂， 生成 Trifluoro-methanesulfonic acid (R)-1-{(4S,5S)-5-[(2R,3R,4S)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-oxo-tetrahydro-furan-2-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester
  参考文献：
  名称：

  Caesium Trifluoroacetate Displacement of Triflates in the Inversion of Alcohols

  摘要：

  与三氟乙酸钠和醋酸铯相比，三氟乙酸铯在通过置换三氟酸盐来有效反转醇的构型方面具有优势。

  DOI：

  10.1055/s-1997-1541