1-adamantanyl 4,6-O-benzylidene-2-O-[3-(4-trifluoromethylphenyl)-prop-2-ynyl]-3-O-benzyl-β-D-mannopyranoside | 1039169-32-8

• 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: 1-adamantanyl 4,6-O-benzylidene-2-O-[3-(4-trifluoromethylphenyl)-prop-2-ynyl]-3-O-benzyl-β-D-mannopyranoside
• 英文别名: (2R,4aR,6S,7S,8S,8aR)-6-(1-adamantyloxy)-2-phenyl-8-phenylmethoxy-7-[3-[4-(trifluoromethyl)phenyl]prop-2-ynoxy]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 1039169-32-8
• 化学式: C₄₀H₄₁F₃O₆
• 分子量: 674.757
• InChiKey: FSHMLXLHRXURFL-SVPFCFSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  49
• 可旋转键数：
  9
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-adamantanyl 4,6-O-benzylidene-2-O-[3-(4-trifluoromethylphenyl)-prop-2-ynyl]-3-O-benzyl-β-D-mannopyranoside 在 氨 、 sodium 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 以72%的产率得到1-adamantanyl 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
• 作为产物：
  描述：

  phenyl 4,6-O-benzylidene-2-O-[3-(4-trifluoromethylphenyl)-prop-2-ynyl]-3-O-benzyl-1-thio-α-D-mannopyranoside 、 1-金刚烷醇 在 4 A molecular sieve 三氟甲磺酸酐 、 sulfobromophthalein sodium 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以72%的产率得到1-adamantanyl 4,6-O-benzylidene-2-O-[3-(4-trifluoromethylphenyl)-prop-2-ynyl]-3-O-benzyl-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.