(2S,3R)-3,6-dihydro-2-methyl-6-(2-propen-1-yl)-3-O-acetyl-2H-pyran-3-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2S,3R)-3,6-dihydro-2-methyl-6-(2-propen-1-yl)-3-O-acetyl-2H-pyran-3-ol
• 英文别名: [(2S,3R)-2-methyl-6-prop-2-enyl-3,6-dihydro-2H-pyran-3-yl] acetate
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: YYQUYDARQNUCRP-UMYMBVSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 、 烯丙基三甲基硅烷 在 gold(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以62%的产率得到(2S,3R)-3,6-dihydro-2-methyl-6-(2-propen-1-yl)-3-O-acetyl-2H-pyran-3-ol
  参考文献：
  名称：

  Scope of AuCl3 in the activation of per-O-acetylglycals

  摘要：

  Gold(III)chloride in catalytic amounts activates 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal, and 3,4-di-O-acetyl-L-rhamnal efficiently. The activated species can be employed in the Ferrier reaction with different nucleophiles at ambient conditions. Attempts have been made to make beta-anomer of the Ferrier product from anomeric-O-propargylated Ferrier product. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.087

文献信息

• Allyl<i>C</i>-Glycosidation of Glycals Mediated by 2,3-Dichloro-5,6-dicyano-<i>p</i>-benzoquinone (DDQ)
  作者：Kazunobu Toshima、Toru Ishizuka、Goh Matsuo、Masaya Nakata

  DOI：10.1246/cl.1993.2013

  日期：1993.12

  A novel and highly stereoselective method for the synthesis of allyl C-glycosides bearing C2-C3 unsaturation has been developed using glycal acetate, allyltrimethylsilane and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) as a neutral activator.

  利用乙酸甘油酯、烯丙基三甲基硅烷和作为中性活化剂的 2,3-二氯-5,6-二氰基对苯醌 (DDQ)，开发出了一种合成具有 C2-C3 不饱和度的烯丙基 C-糖苷的新型高立体选择性方法。
• In(OTf)₃—A New Efficient Lewis Acid Catalyst for Stereoselective C-Glycosylation Reactions of Glycal Derivatives
  作者：Rina Ghosh、Arijit Chakraborty、Dilip K. Maiti

  DOI：10.1081/scc-120018923

  日期：2003.1.6

  A variety of glycal derivatives reacted smoothly with allyltrimethylsilane and trimethylsilylcyanide in neat condition as well as in dichloromethane in the presence of 2-5 mol% of In(OTf)(3) affording the corresponding 2,3-unsaturated C-glycosides in excellent yields and moderate to excellent alpha-selectivities.