1,2-O-(1-甲基乙亚基)-alpha-L-吡喃山梨糖 | 18604-34-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,2-O-(1-甲基乙亚基)-alpha-L-吡喃山梨糖
• 英文名称: 1,2-O-Isopropylidine-α-L-sorbopyranose
• 英文别名: 1,2-O-isopropylidene-α-L-sorbopyranose；1,2-isopropylidene-α-L-sorbopyranose；1,2-O-Isopropyliden-α,L-sorbopyranose；1,2-O-Isopropyliden-α-L-sorbopyranose；1.2-O-Isopropyliden-α-L-sorbopyranose；1,2-O-Isopropyliden-L-sorbopyranose；alpha-l-Sorbopyranose, 1,2-O-(1-methylethylidene)-；(5S,6S,7R,8S)-2,2-dimethyl-1,3,10-trioxaspiro[4.5]decane-6,7,8-triol
• CAS: 18604-34-7
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: NCPKAWHTYZABFG-XQXXSGGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  1,2-O-(1-甲基乙亚基)-alpha-L-吡喃山梨糖 在 sodium hydroxide 、 硫酸 、 四丁基硫酸氢铵 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 56.42h， 生成 L-Fructose
  参考文献：
  名称：

  Application of a phase transfer reaction to the synthesis of l-fructose

  摘要：

  L-Fructose was prepared in five steps from L-sorbose (1). 1,2-O-Isopropylidene-alpha-L-sorbopyranose (2), prepared from 1, was selectively tosylated using phase transfer catalysis to give 1,2-O-isopropylidene-3-O- (p-tolylsulfonyl)-alpha-L-sorbopyranose (3). Formation of a 3,4-anhydro ring, followed by its base-catalyzed opening to effect overall inversion of configuration at both C-3 and C-4 gave 1,2-O-isopropylidene-alpha-L-fructopyranose (5), which was deacetonated to yield L-fructose (6).

  DOI：

  10.1016/0008-6215(94)00255-e
• 作为产物：
  描述：

  L-sorbopyranose 、 丙酮 在 copper(II) sulfate 作用下， 反应 5.0h， 以40%的产率得到1,2-O-(1-甲基乙亚基)-alpha-L-吡喃山梨糖
  参考文献：
  名称：

  Application of a phase transfer reaction to the synthesis of l-fructose

  摘要：

  L-Fructose was prepared in five steps from L-sorbose (1). 1,2-O-Isopropylidene-alpha-L-sorbopyranose (2), prepared from 1, was selectively tosylated using phase transfer catalysis to give 1,2-O-isopropylidene-3-O- (p-tolylsulfonyl)-alpha-L-sorbopyranose (3). Formation of a 3,4-anhydro ring, followed by its base-catalyzed opening to effect overall inversion of configuration at both C-3 and C-4 gave 1,2-O-isopropylidene-alpha-L-fructopyranose (5), which was deacetonated to yield L-fructose (6).

  DOI：

  10.1016/0008-6215(94)00255-e

文献信息

• A new method of acetonation with the zeolite HY as catalyst. Synthesis of O-Isopropylidene sugar derivatives
  作者：Amélia P. Rauter、Fernando Ramôa-Ribeiro、Ana C. Fernandes、JoséA. Figueiredo

  DOI：10.1016/0040-4020(95)00291-f

  日期：1995.6

  D-glucofuranurono-6,3-lactone, D-ribose and its methyl glycoside led to the formation of di-O- and/or mono-O-isopropylidene derivatives in yields from 37–75%. Reaction with D-galactose and L-arabinose afforded the synthesis of the corresponding furanose derivatives as major products, together with minor quantities of the thermodynamically more stable pyranose derivatives.

  事实证明，沸石HY是糖类丙酮化的合适催化剂。该方法由非常简单且经济的实验程序组成，其中催化剂可以回收并且可以再生。与D-半乳糖，L-阿拉伯糖，D-葡萄糖，D-木糖，L-山梨糖，D-葡萄糖呋喃呋喃诺-6,3-内酯，D-核糖及其甲基糖苷反应导致形成di- O-和/或单-O-异亚丙基衍生物的产率为37-75％。与D-半乳糖和L-阿拉伯糖的反应提供了相应的呋喃糖衍生物作为主要产物的合成，以及少量的热力学更稳定的吡喃糖衍生物。
• Chemical reaction mechanism in acetonation of L-sorbose
  作者：I. D. Chapanov、V. A. Nikiforov、V. V. Zarutskii、A. A. Orekhov

  DOI：10.1007/bf00765390

  日期：1981.10
• ENZYMATIC O-GALACTOSYLATION OF SELECTED FREE AS WELL AS PARTIALLY PROTECTED KETOHEXOSES
  作者：Brigitte Eder、Inge Lundt、Arnold Stütz、Tanja Wrodnigg

  DOI：10.1081/car-100108279

  日期：——

  A range of partially protected ketoses was O-galactosylated with P-galactosidase from Aspergillus oryzae employing (4-nitro)phenyl beta -D-galactopyranoside as the donor. This enzyme also accepted free D-tagatose as a substrate.