1-O-acetyl-2,3-O-isopropylidene-α-L-sorbofuranose | 58794-59-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-acetyl-2,3-O-isopropylidene-α-L-sorbofuranose
• 英文别名: [(3aS,5S,6R,6aS)-6-hydroxy-5-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-5H-furo[2,3-d][1,3]dioxol-3a-yl]methyl acetate
• CAS: 58794-59-5
• 化学式: C₁₁H₁₈O₇
• 分子量: 262.26
• InChiKey: MTCBEANCIJJYJP-DKIAZLNASA-N

物化性质

• 沸点：
  405.9±40.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-2,3-O-isopropylidene-α-L-sorbofuranose 在 吡啶 、 盐酸 、 偶氮二甲酸二异丙酯 、 碳酸氢钠 、 三苯基膦 作用下， 以 四氢呋喃 、 乙二醇甲醚 、 水 为溶剂， 反应 148.0h， 生成 methyl 1,4-anhydro-6-O-mesyl-1-thio-β-L-psicofuranoside
  参考文献：
  名称：

  Preparation of Anhydro-Thiohexopyranosides and -Thiohexofuranosides with D-fructo-, L-sorbo-, L-psico- and L-tagato-Configuration Starting from L-Sorbose

  摘要：

  Methyl alpha- L-sorbopyranoside is transformed into the bicyclic thiosugar methyl 1,5-anhydro-3,4-di-O-mesyl-1-thio-beta-D-fructopyranoside in two steps, whereas the corresponding 3-O-benzoate is obtained from methyl 1,3-O-benzylidene-alpha-L-sorbopyranoside in three steps. 2,3-O-Isopropylidenesorbofuranosides, on the other hand, can be transformed into 6-S-thioacetates by use of the thio-Mitsunobu reaction. These are suitable precursors for the preparation of 1,6-anhydro-1-thiosorbofuranosides. Also, methyl 1-S-acetyl-1-thio-L-sorbofuranosides with mesylate leaving groups are available by the thio-Mitsunobu reaction. They yield 1,4-anhydro-1-thio-beta-L-tagatofuranosides, 1,3-anhydro-alpha-L-psicofuranosides and 1,6-anhydro-1-thio-alpha-L-sorbofuranosides depending on the configuration of the starting compound. Attempts to prepare azido-thio-sugars by displacement of mesylate groups with alkali metal azides failed.

  DOI：

  10.1080/10426500701340915
• 作为产物：
  描述：

  1-O-acetyl-2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose 在 溶剂黄146 作用下， 反应 1.0h， 以91%的产率得到1-O-acetyl-2,3-O-isopropylidene-α-L-sorbofuranose
  参考文献：
  名称：

  Preparation of Anhydro-Thiohexopyranosides and -Thiohexofuranosides with D-fructo-, L-sorbo-, L-psico- and L-tagato-Configuration Starting from L-Sorbose

  摘要：

  Methyl alpha- L-sorbopyranoside is transformed into the bicyclic thiosugar methyl 1,5-anhydro-3,4-di-O-mesyl-1-thio-beta-D-fructopyranoside in two steps, whereas the corresponding 3-O-benzoate is obtained from methyl 1,3-O-benzylidene-alpha-L-sorbopyranoside in three steps. 2,3-O-Isopropylidenesorbofuranosides, on the other hand, can be transformed into 6-S-thioacetates by use of the thio-Mitsunobu reaction. These are suitable precursors for the preparation of 1,6-anhydro-1-thiosorbofuranosides. Also, methyl 1-S-acetyl-1-thio-L-sorbofuranosides with mesylate leaving groups are available by the thio-Mitsunobu reaction. They yield 1,4-anhydro-1-thio-beta-L-tagatofuranosides, 1,3-anhydro-alpha-L-psicofuranosides and 1,6-anhydro-1-thio-alpha-L-sorbofuranosides depending on the configuration of the starting compound. Attempts to prepare azido-thio-sugars by displacement of mesylate groups with alkali metal azides failed.

  DOI：

  10.1080/10426500701340915

文献信息

• Thermodynamic and kinetic considerations in the chemoselective O-acylation by mixed anhydrides. A semiempirical MO approach
  作者：Antonio J. Mota、Rafael Robles、Luis Álvarez de Cienfuegos、Alberto Lamenca

  DOI：10.1016/j.tetlet.2004.03.045

  日期：2004.4

  A simple methodology to achieve high chemoselective O-acylation of primary hydroxy groups, in the presence of secondary ones, was performed by means of the quick generation of a mixed anhydride using mild and inexpensive conditions. Steric and electronic factors are involved in this preference. As far as the geometries are concerned, semiempirical calculations were carried out in order to determine

  通过在温和且廉价的条件下快速生成混合酸酐，可以实现一种简单的方法，可在仲羟基存在下实现伯羟基的高化学选择性O-酰化。优先考虑电子和立体因素。就几何形状而言，进行了半经验计算，以确定对热力学和动力学的贡献的性质。从定性的角度，发现热力学是糖依赖性的，而动力学是混合酸酐的依赖性的。这些结论与实验结果非常吻合，因为可以用相同的方式对不同的系统进行建模，因此可以将半经验MO计算用作调节此过程选择性比的工具。
• A reinvestigation of the synthesis and revision of spectral data of 1,2-O-isopropylidene-α-l-sorbofuranose, 1,2:4,6-di-O-isopropylidene-α-l-sorbofuranose and derivatives
  作者：Anna Biela-Banaś、Estelle Gallienne、Olivier R. Martin

  DOI：10.1016/j.carres.2013.05.019

  日期：2013.10

  di-O-isopropylidene-l-sorbofuranose derivatives are important starting materials for the synthesis of modified sugars and useful chiral compounds. However, several inconsistencies in the spectral data of these compounds and erroneous structural assignments have been noted in the literature. The unambiguous synthesis of 1,2:4,6-di-O-isopropylidene-alpha-L-sorbofuranose and derivatives of 1,2- and 2,3-O-isopro

  单-和二-O-异亚丙基-1-山梨糖呋喃糖衍生物是合成修饰的糖和有用的手性化合物的重要起始原料。然而，在文献中已经注意到这些化合物的光谱数据中的一些不一致和错误的结构分配。1,2,4,6-二-O-异亚丙基-α-L-山梨糖醛酸和1,2-和2,3-O-异亚丙基-α-L-山梨糖醛酸酶衍生物的明确合成已实现，并且确定的光谱提供了有关这些化合物的数据。