4-methylphenyl 4,6-O-isopropylidene-1-thio-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylphenyl 4,6-O-isopropylidene-1-thio-β-D-glucopyranoside
• 英文别名: 4-Methylphenyl 4,6-O-isopropylidene-1-thio-beta-D-glucopyranoside min.；(4aR,6S,7R,8R,8aS)-2,2-dimethyl-6-(4-methylphenyl)sulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• 化学式: C₁₆H₂₂O₅S
• 分子量: 326.414
• InChiKey: NFVMLWMNJOOWJW-RYPNDVFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  93.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-甲氧基丙烯 、 1-硫代-b-甲基葡萄糖甙-4-甲基苯酯 在 vanadyl triflate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以82%的产率得到4-methylphenyl 4,6-O-isopropylidene-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  O-Isopropylidenation of carbohydrates catalyzed by vanadyl triflate

  摘要：

  Vanadyl triflate has been identified as a mild and efficient catalyst for the chemoselective O-isopropylidenation of functionalized carbohydrates with acetone and acetone equivalents. The current protocol is compatible with a diverse array of protecting groups and the products can be readily isolated by simple aqueous wash. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.001

文献信息

• Nano<i>n</i>-Propylsulfonated Magnetic γ-Fe₂O₃as an Efficient and Reusable Catalyst for the Synthesis<i>O</i>-Isopropylidene Derivatives of Carbohydrates
  作者：Xiaoran Zhang、Changqiang Zhang

  DOI：10.1080/07328303.2013.804082

  日期：2013.5.4

  Nano n-propylsulfonated -Fe2O3 was found to be a highly efficient, reusable heterogeneous catalyst for the conversion of a range of monosaccharides and some of their derivatives to the corresponding O-isopropylidene derivatives in good to excellent yields by refluxing the reaction mixture in dry acetone. The magnetic property of the catalyst enabled its separation from the reaction mixture by a simple process of filtration along with the aid of an external magnet. The efficiency of the catalyst was found to be largely unaffected for at least up to six cycles of reuse, thus proving the new methodology to be environmentally rewarding besides being simple and facile in operation.
• O-Isopropylidenation of carbohydrates catalyzed by vanadyl triflate
  作者：Chun-Cheng Lin、Mi-Dan Jan、Shiue-Shien Weng、Chang-Ching Lin、Chien-Tien Chen

  DOI：10.1016/j.carres.2006.04.001

  日期：2006.8

  Vanadyl triflate has been identified as a mild and efficient catalyst for the chemoselective O-isopropylidenation of functionalized carbohydrates with acetone and acetone equivalents. The current protocol is compatible with a diverse array of protecting groups and the products can be readily isolated by simple aqueous wash. (c) 2006 Elsevier Ltd. All rights reserved.