Pent-4-enyl 2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranoside | 113533-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: Pent-4-enyl 2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranoside
• CAS: 113533-83-8；113533-84-9
• 化学式: C₂₂H₂₈O₈
• 分子量: 420.46
• InChiKey: VZGBBTSFZRFAHE-KGBKIKGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Pent-4-enyl 2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 乙腈 为溶剂， 反应 36.0h， 以62%的产率得到4,6-O-benzylidene-2,3-di-O-acetyl-D-glucopyranose
  参考文献：
  名称：

  n-Pentenyl glycosides permit the chemospecific liberation of the anomeric center

  摘要：

  DOI：

  10.1021/ja00216a057

文献信息

• n-Pentenyl Glycoside Based Methodology for Determining the Relative Reactivities of Variously Protected Pairs of Glycosides
  作者：Bruce G. Wilson、Bert Fraser-Reid

  DOI：10.1021/jo00107a008

  日期：1995.1

  The relative rate of hydrolysis of an alpha/beta anomeric pair of glycosides is generally considered to provide insight into various factors that influence anomeric reactivity. However the fact that such hydrolyses are usually carried out with aqueous acids severely limits the range of substrates that can studied. This limitation is overcome with n-pentenyl glycosides (NPGs) which are hydrolyzed under neutral, oxidative conditions. A procedure is described in which a pair (e.g. alpha(1)/beta(1), alpha(1)/beta(2), beta(1)/beta(2), etc.) of NPGs is made to compete for an insufficient amount of N-bromosuccinimide, the relative rates of reaction being determined from HPLC peak heights of the unreacted starting materials. Some commonly used acid labile protecting groups, e.g. cyclic acetals and acetyl, are shown to exert profound effects upon relative and absolute rates of anomeric activation.