methyl (1S,2R,3S)-3-tert-butyldimethylsilyloxy-2-(5-2'-tetrahydropyranyloxy-cis-2-pentenyl)-1-cyclopentaneacetate | 223448-70-2

• 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: methyl (1S,2R,3S)-3-tert-butyldimethylsilyloxy-2-(5-2'-tetrahydropyranyloxy-cis-2-pentenyl)-1-cyclopentaneacetate
• CAS: 223448-70-2
• 化学式: C₂₄H₄₄O₅Si
• 分子量: 440.696
• InChiKey: QIWGJENNBIUVCL-LUAXISGOSA-N

物化性质

• 沸点：
  475.092±40.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.007±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R,3S)-3-tert-butyldimethylsilyloxy-2-(5-2'-tetrahydropyranyloxy-cis-2-pentenyl)-1-cyclopentaneacetate 在 二甲基氯化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 4.0h， 以70%的产率得到methyl (1S,2R,3S)-3-tert-butyldimethylsilyloxy-2-(5-hydroxy-cis-2-pentenyl)-1-cyclopentaneacetate
  参考文献：
  名称：

  Synthesis of both the enantiomers of methyl tuberonate, natural methyl β-d-glucopyranosyloxyjasmonate and its epimer

  摘要：

  Synthesis of both the enantiomers of methyl tuberonate 3, natural methyl beta-D-glucopyranosyloxyjasmonate 6, and its epimer, methyl beta-D-glucopyranosyl-tuberonate 5 is described. They were synthesized via mild deprotection of dichloroacetate and trifluoroacetate by methanolysis from the enantiomerically pure dithiane 9. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00157-x
• 作为产物：
  描述：

  (1S,5S,8R)-8-(5-2'-tetrahydropyranyloxy-cis-2-pentenyl)-2-oxabicyclo<3.2.1>octan-3-one 在 咪唑 、 氢氧化钾 作用下， 以 甲醇 、 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 methyl (1S,2R,3S)-3-tert-butyldimethylsilyloxy-2-(5-2'-tetrahydropyranyloxy-cis-2-pentenyl)-1-cyclopentaneacetate
  参考文献：
  名称：

  Synthesis of both the enantiomers of methyl tuberonate, natural methyl β-d-glucopyranosyloxyjasmonate and its epimer

  摘要：

  Synthesis of both the enantiomers of methyl tuberonate 3, natural methyl beta-D-glucopyranosyloxyjasmonate 6, and its epimer, methyl beta-D-glucopyranosyl-tuberonate 5 is described. They were synthesized via mild deprotection of dichloroacetate and trifluoroacetate by methanolysis from the enantiomerically pure dithiane 9. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00157-x