O-(+)-borneyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 1119240-84-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: O-(+)-borneyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: (+)-bornyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• CAS: 1119240-84-4
• 化学式: C₂₀H₃₀O₆
• 分子量: 366.455
• InChiKey: RXMBNYVFPUFVMR-MILRCDJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (+)-冰片 、 乙酰化葡萄烯糖 在 zinc dibromide 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以87%的产率得到O-(+)-borneyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  ZnBr₂-Catalyzed and Microwave-Assisted Synthesis of 2,3-Unsaturated Glucosides of Hindered Phenols and Alcohols

  摘要：

  DOI：

  10.1080/00397911.2014.909490

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.