methyl 1,3,4,6-tetra-O-acetyl-α-D-fructofuranoside | 70802-04-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 1,3,4,6-tetra-O-acetyl-α-D-fructofuranoside
• 英文别名: methyl α-D-fructofuranoside peracetate；methyl α-D-fructofuranoside；methyl-(tetra-O-acetyl-α-D-fructofuranoside)；Methyl-(tetra-O-acetyl-α-D-fructofuranosid)
• CAS: 70802-04-9
• 化学式: C₁₅H₂₂O₁₀
• 分子量: 362.334
• InChiKey: ANHUZKQOGGBSEF-KBXIAJHMSA-N

物化性质

• 沸点：
  423.9±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.28
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 1,3,4,6-tetra-O-acetyl-α-D-fructofuranoside 在 二氯二茂锆 、 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 生成 、 methyl 1,3,4-tri-O-acetyl-α-D-fructofuranoside
  参考文献：
  名称：

  Regio- and Chemoselective Deprotection of Primary Acetates by Zirconium Hydrides

  摘要：

  A combination of DIBAL-H and Cp2ZrCl2 is shown to promote the regioselective cleavage of primary acetates on a broad scope of substrates, ranging from carbohydrates to terpene derivatives, with a high tolerance toward protecting groups and numerous functionalities found in natural products and bioactive compounds. Apart from providing highly valuable building blocks in only two steps from biosourced raw materials, this selective de-O-acetylation should also be strongly helpful to solve selectivity issues in organic synthesis.

  DOI：

  10.1021/acs.orglett.8b03947
• 作为产物：
  描述：

  D-fructose 在 吡啶 、 乙酰氯 作用下， 反应 36.0h， 生成 methyl 1,3,4,6-tetra-O-acetyl-α-D-fructofuranoside
  参考文献：
  名称：

  合成唾液酸核苷模拟物的方法

  摘要：

  描述了一种基于d-果糖合成新型唾液酸核苷模拟物的方法。这些模拟物的合成可通过七个步骤以良好的总收率实现。关键的合成步骤是嘧啶碱基（尿嘧啶，5-氟尿嘧啶和胞嘧啶）与修饰的d-tagato果糖呋喃糖苷的C-1位置偶联。

  DOI：

  10.1016/j.tetasy.2005.01.035

文献信息

• Acetalation of sucrose by acetal exchange with concomitant fission of the glycosidic bond. Some new acetals of<scp>D</scp>-glucose and methyl α-<scp>D</scp>-fructofuranoside
  作者：Raul Cortes-Garcia、Leslie Hough、Anthony C. Richardson

  DOI：10.1039/p19810003176

  日期：——

  Prolonged reaction of sucrose with 2,2-dimethoxypropane in NN-dimethylformamide in the presence of toluene-p-sulphonic acid (0.3% w/v) afforded, after acetylation, methyl 4,6-di-O-acetyl-1,3-O-isopropylidene-α-D-fructofuranoside together with four acetals of D-glucose, namely, (1S)-1-methoxy-1,2:3,4:5,6-tri-O-isopropylidene-D-glucitol, 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, 3-O-acetyl-1

  乙酰化后，在甲苯-对-磺酸（0.3％w / v）存在下，蔗糖与2,2-二甲氧基丙烷在NN-二甲基甲酰胺中的长时间反应，得到甲基4,6-二-O-乙酰基-1,3 - ö异亚丙基α- d -fructofuranoside与四个缩醛一起d葡萄糖，即，（1个小号）-1-甲氧基-1,2-：3,4：5,6-三ö异亚丙基d -葡萄糖醇，3 - O-乙酰基-1,2：5,6-二-O-异亚丙基-α - D-葡萄糖呋喃糖，3 - O-乙酰基-1,2：4,6-二-O-异亚丙基-α- d-吡喃葡萄糖和1,2,3-三-O-乙酰基-4,6 - O-异亚丙基-αβ- D-吡喃葡萄糖。讨论了这些化合物的形成机理。甲基α-和β- D-果糖呋喃糖苷的几种衍生物已经由甲基1，3 - O-异亚丙基-α- D-果糖呋喃糖苷制备。
• Verhart, Cor G.J.; Fransen, Carel T.M.; Zwanenburg, Binne, Recueil des Travaux Chimiques des Pays-Bas, 1996, vol. 115, # 2, p. 133 - 139
  作者：Verhart, Cor G.J.、Fransen, Carel T.M.、Zwanenburg, Binne、Chittenden, Gordon J.F.

  DOI：——

  日期：——
• Schlubach; Bartels, Justus Liebigs Annalen der Chemie, 1939, vol. 541, p. 76,83
  作者：Schlubach、Bartels

  DOI：——

  日期：——
• The Analysis of Gamma-Fructoside Mixtures by Means of Invertase. V. Methylated and Acetylated Derivatives of Crystalline α-Methyl- and α-Benzylfructofuranoside¹
  作者：C. B. Purves、C. S. Hudson

  DOI：10.1021/ja01280a012

  日期：1937.1
• Regio- and Chemoselective Deprotection of Primary Acetates by Zirconium Hydrides
  作者：Marine Gavel、Thibaut Courant、Antoine Yvan Philippe Joosten、Thomas Lecourt

  DOI：10.1021/acs.orglett.8b03947

  日期：2019.4.5

  A combination of DIBAL-H and Cp2ZrCl2 is shown to promote the regioselective cleavage of primary acetates on a broad scope of substrates, ranging from carbohydrates to terpene derivatives, with a high tolerance toward protecting groups and numerous functionalities found in natural products and bioactive compounds. Apart from providing highly valuable building blocks in only two steps from biosourced raw materials, this selective de-O-acetylation should also be strongly helpful to solve selectivity issues in organic synthesis.