cyclooctanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 1119240-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: cyclooctanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-cyclooctyloxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1119240-76-4
• 化学式: C₁₈H₂₈O₆
• 分子量: 340.417
• InChiKey: VRFOUIXKKGAMDA-KSZLIROESA-N

物化性质

• 沸点：
  437.0±45.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  环辛醇 、 乙酰化葡萄烯糖 在 aluminum oxide 、 zinc(II) chloride 作用下， 反应 0.33h， 以82%的产率得到cyclooctanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  ZnCl2/alumina impregnation catalyzed Ferrier rearrangement: an expedient synthesis of pseudoglycosides

  摘要：

  An improved method for the synthesis of 2,3-unsaturated-O-glycosides has been developed. ZnCl2 impregnated on activated alumina acts as an excellent reagent system for the conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated-O-glycosides with high alpha-selectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.099

文献信息

• A convenient synthesis of pseudoglycosides via a Ferrier-type rearrangement using metal-free H3PO4 catalyst
  作者：Bala Kishan Gorityala、Shuting Cai、Rujee Lorpitthaya、Jimei Ma、Kalyan Kumar Pasunooti、Xue-Wei Liu

  DOI：10.1016/j.tetlet.2008.11.103

  日期：2009.2

  A mild and efficient synthesis of pseudoglycals has been developed using a metal-free catalytic system. Phosphoric acid proved to be an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-D-glycal to 2,3-unsaturated O-glycosides. A wide range of alcohols including naturally bioactive compounds could be coupled with the glycal to give the desired products in good to excellent yields and with high levels of alpha-selectivity. (C) 2008 Elsevier Ltd. All rights reserved.