n-octyl 2,3-di-O-benzyl-β-D-fucofuranoside | 1000874-32-7

• 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: n-octyl 2,3-di-O-benzyl-β-D-fucofuranoside
• 英文别名: (1R)-1-[(2S,3S,4R,5R)-5-octoxy-3,4-bis(phenylmethoxy)oxolan-2-yl]ethanol
• CAS: 1000874-32-7
• 化学式: C₂₈H₄₀O₅
• 分子量: 456.623
• InChiKey: TYPJVECNYGMIGS-IVMOBWQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  n-octyl 2,3-di-O-benzyl-β-D-fucofuranoside 在 palladium diacetate 氢气 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 以100%的产率得到n-octyl β-D-fucofuranoside
  参考文献：
  名称：

  Versatile Synthesis of Rare Nucleotide Furanoses

  摘要：

  Direct activation of unprotected thioimidoyl furanosides yielded in only one step and few minutes a panel of rare uridine 5'-diphosphofuranoses. Diastereoselectivity of the reaction was tightly connected with reaction time, temperature, and nature of the furanosyl donor. This approach was totally selective since no ring expansion from the initial five-membered ring to the more stable pyranose form was observed.

  DOI：

  10.1021/ol702392x
• 作为产物：
  描述：

  n-octyl 2,3-di-O-benzyl-5,6-O-sulfonyl-β-D-galactofuranoside 在 sodium tetrahydroborate 、 硫酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以88%的产率得到n-octyl 2,3-di-O-benzyl-β-D-fucofuranoside
  参考文献：
  名称：

  Versatile Synthesis of Rare Nucleotide Furanoses

  摘要：

  Direct activation of unprotected thioimidoyl furanosides yielded in only one step and few minutes a panel of rare uridine 5'-diphosphofuranoses. Diastereoselectivity of the reaction was tightly connected with reaction time, temperature, and nature of the furanosyl donor. This approach was totally selective since no ring expansion from the initial five-membered ring to the more stable pyranose form was observed.

  DOI：

  10.1021/ol702392x

文献信息

• Versatile Synthesis of Rare Nucleotide Furanoses
  作者：Pauline Peltier、Richard Daniellou、Caroline Nugier-Chauvin、Vincent Ferrières

  DOI：10.1021/ol702392x

  日期：2007.12.1

  Direct activation of unprotected thioimidoyl furanosides yielded in only one step and few minutes a panel of rare uridine 5'-diphosphofuranoses. Diastereoselectivity of the reaction was tightly connected with reaction time, temperature, and nature of the furanosyl donor. This approach was totally selective since no ring expansion from the initial five-membered ring to the more stable pyranose form was observed.