2-(allyloxy)ethanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 1178562-97-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(allyloxy)ethanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• CAS: 1178562-97-4
• 化学式: C₁₅H₂₂O₇
• 分子量: 314.335
• InChiKey: PEATVVLBCCBICD-ZNMIVQPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  22.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  烯丙基羟乙基醚 、 乙酰化葡萄烯糖 在 aluminum oxide 、 zinc(II) chloride 作用下， 反应 0.5h， 以78%的产率得到2-(allyloxy)ethanyl 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

• (S)-Camphorsulfonic acid catalyzed highly stereoselective synthesis of pseudoglycosides
  作者：Bala Kishan Gorityala、Shuting Cai、Jimei Ma、Xue-Wei Liu

  DOI：10.1016/j.bmcl.2009.04.003

  日期：2009.6

  A mild and efficient synthesis of pseudoglycosides has been developed using metal free (S)-camphorsulfonic acid. (S)-CSA acts as an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated O-glycosides. A wide range of biologically active natural products, alcohols and thiols could be coupled with glucal to give the desired pseudoglycosides in good to excellent yields with exclusive alpha-stereoselectivity. (C) 2009 Elsevier Ltd. All rights reserved.