Trifluoro-methanesulfonic acid (R)-1-[(2S,3S,4R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-oxo-tetrahydro-furan-2-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester | 198420-86-9

• 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-[(2S,3S,4R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-oxo-tetrahydro-furan-2-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester
• 英文别名: [(1R)-1-[(2S,3S,4R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-oxooxolan-2-yl]-2-[tert-butyl(dimethyl)silyl]oxyethyl] trifluoromethanesulfonate
• CAS: 198420-86-9
• 化学式: C₂₅H₅₁F₃O₈SSi₃
• 分子量: 652.993
• InChiKey: MODAJPVBFHLHBN-YSTOQKLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.95
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (R)-1-[(2S,3S,4R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-oxo-tetrahydro-furan-2-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester 在 甲醇 、 氧化汞红 、 potassium carbonate 作用下， 生成 (3R,4S,5S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-dihydro-furan-2-one
  参考文献：
  名称：

  Triazole carboxylic acids as anionic sugar mimics? Inhibition of glycogen phosphorylase by a d-glucotriazole carboxylate

  摘要：

  Triazole-carboxylic acids related to D-glucose and D-galactose may be prepared by intramolecular [1,3]-dipolar cycloadditions of azides to unsaturated esters, followed by bromine oxidation of the resulting triazoline. Such materials may provide a series of anionic mimics of carbohydrates. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00561-2
• 作为产物：
  描述：

  2,3-di-O-tert-butyldimethylsilyl-5,6-O-isopropylidene-D-glucono-1,4-lactone 在 吡啶 、 咪唑 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 生成 Trifluoro-methanesulfonic acid (R)-1-[(2S,3S,4R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-oxo-tetrahydro-furan-2-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester
  参考文献：
  名称：

  Triazole carboxylic acids as anionic sugar mimics? Inhibition of glycogen phosphorylase by a d-glucotriazole carboxylate

  摘要：

  Triazole-carboxylic acids related to D-glucose and D-galactose may be prepared by intramolecular [1,3]-dipolar cycloadditions of azides to unsaturated esters, followed by bromine oxidation of the resulting triazoline. Such materials may provide a series of anionic mimics of carbohydrates. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00561-2

文献信息

• Caesium Trifluoroacetate Displacement of Triflates in the Inversion of Alcohols
  作者：Andrew Bell、Lea Pickering、Malcolm Finn、Carmen de la Fuente、Thomas Krülle、Benjamin Davis、G. Fleet

  DOI：10.1055/s-1997-1541

  日期：1997.9

  Caesium trifluoroacetate has advantages over both sodium trifluoroacetate and caesium acetate for the efficient inversion of configuration of alcohols by displacement of triflates.

  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。
• Triazole carboxylic acids as anionic sugar mimics? Inhibition of glycogen phosphorylase by a d-glucotriazole carboxylate
  作者：Thomas M. Krülle、Carmen de la Fuente、Lea Pickering、Robin T. Aplin、Katerina E. Tsitsanou、Spyros E. Zographos、Nikos G. Oikonomakos、Robert J. Nash、Rhodri C. Griffiths、George W.J. Fleet

  DOI：10.1016/s0957-4166(97)00561-2

  日期：1997.11

  Triazole-carboxylic acids related to D-glucose and D-galactose may be prepared by intramolecular [1,3]-dipolar cycloadditions of azides to unsaturated esters, followed by bromine oxidation of the resulting triazoline. Such materials may provide a series of anionic mimics of carbohydrates. (C) 1997 Elsevier Science Ltd.