1-adamantanyl 3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside | 1039169-49-7

• 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: 1-adamantanyl 3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside
• 英文别名: (2R,4aR,6S,7S,8R,8aR)-6-(1-adamantyloxy)-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 1039169-49-7
• 化学式: C₃₀H₃₆O₆
• 分子量: 492.612
• InChiKey: LDXGELOEONXQJS-OQLRHYQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-adamantanyl 4,6-O-benzylidene-2-O-[3-(4-trifluoromethylphenyl)-prop-2-ynyl]-3-O-benzyl-β-D-mannopyranoside 在 naphthalen-1-yl-lithium 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以85%的产率得到1-adamantanyl 3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside
  参考文献：
  名称：

  Application of the 4-Trifluoromethylbenzenepropargyl Ether Group as an Unhindered, Electron Deficient Protecting Group for Stereoselective Glycosylation

  摘要：

  4-Trifluoromethylbenzenepropargyl ethers are stable and sterically minimal alcohol protecting groups that are readily cleaved in a single step by exposure to lithium naphthalenide. In conjunction with the 4,6-O-benzylidene protecting group, glycosylation reactions of 2-O-(4-trifluoromethylbenzenepropargyl)-protected mannosyl donors are extremely beta-selective.

  DOI：

  10.1021/jo7023398

文献信息

• Application of the 4-Trifluoromethylbenzenepropargyl Ether Group as an Unhindered, Electron Deficient Protecting Group for Stereoselective Glycosylation
  作者：David Crich、Maheswaran S. Karatholuvhu

  DOI：10.1021/jo7023398

  日期：2008.7.1

  4-Trifluoromethylbenzenepropargyl ethers are stable and sterically minimal alcohol protecting groups that are readily cleaved in a single step by exposure to lithium naphthalenide. In conjunction with the 4,6-O-benzylidene protecting group, glycosylation reactions of 2-O-(4-trifluoromethylbenzenepropargyl)-protected mannosyl donors are extremely beta-selective.