1-nonen-4S-yl 3-O-benzyl-2-O-tert-butyldimethylsilyl-β-D-fucopyranoside | 1130996-40-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-nonen-4S-yl 3-O-benzyl-2-O-tert-butyldimethylsilyl-β-D-fucopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-5-[tert-butyl(dimethyl)silyl]oxy-2-methyl-6-[(4S)-non-1-en-4-yl]oxy-4-phenylmethoxyoxan-3-ol
• CAS: 1130996-40-5
• 化学式: C₂₈H₄₈O₅Si
• 分子量: 492.772
• InChiKey: PMVQKXQTVDMJPA-GLZMQPIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-nonen-4S-yl 3-O-benzyl-2-O-tert-butyldimethylsilyl-β-D-fucopyranoside 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 1-nonen-4S-yl 4-O-acetyl-3-O-benzyl-2-O-tert-butyldimethylsilyl-β-D-fucopyranoside
  参考文献：
  名称：

  Total Synthesis of Ipomoeassin F

  摘要：

  The first total synthesis of ipomoeassin F was carried out using a convergent approach that relied upon the use of Schmidt glycosidation technology for the coupling of two suitably protected monosaccharide fragments. After two steps, ring-closing metathesis was used to form the macrocyclic ring, and seven more steps then furnished ipomoeassin F. In vitro inhibitory activity against a four-panel cell line showed low nanomolar inhibitory activity.

  DOI：

  10.1021/ol900086b
• 作为产物：
  描述：

  1-nonen-4S-yl 3-O-benzyl-β-D-fucopyranoside 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到1-nonen-4S-yl 3-O-benzyl-2-O-tert-butyldimethylsilyl-β-D-fucopyranoside
  参考文献：
  名称：

  Total Synthesis of Ipomoeassin F

  摘要：

  The first total synthesis of ipomoeassin F was carried out using a convergent approach that relied upon the use of Schmidt glycosidation technology for the coupling of two suitably protected monosaccharide fragments. After two steps, ring-closing metathesis was used to form the macrocyclic ring, and seven more steps then furnished ipomoeassin F. In vitro inhibitory activity against a four-panel cell line showed low nanomolar inhibitory activity.

  DOI：

  10.1021/ol900086b

文献信息

• Total Synthesis of Ipomoeassin F
  作者：Maarten H. D. Postema、Karen TenDyke、James Cutter、Galina Kuznetsov、Qunli Xu

  DOI：10.1021/ol900086b

  日期：2009.3.19

  The first total synthesis of ipomoeassin F was carried out using a convergent approach that relied upon the use of Schmidt glycosidation technology for the coupling of two suitably protected monosaccharide fragments. After two steps, ring-closing metathesis was used to form the macrocyclic ring, and seven more steps then furnished ipomoeassin F. In vitro inhibitory activity against a four-panel cell line showed low nanomolar inhibitory activity.