5-[(2S,4S,5S)-tetrahydro-4-hydroxy-5-hydroxymethyl-2-furanyl]-2-pentyn-1-yl t-butyldimethylsilyl ether | 629614-51-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[(2S,4S,5S)-tetrahydro-4-hydroxy-5-hydroxymethyl-2-furanyl]-2-pentyn-1-yl t-butyldimethylsilyl ether
• 英文别名: (2S,3S,5S)-5-[5-[tert-butyl(dimethyl)silyl]oxypent-3-ynyl]-2-(hydroxymethyl)oxolan-3-ol
• CAS: 629614-51-3
• 化学式: C₁₆H₃₀O₄Si
• 分子量: 314.497
• InChiKey: RNXAVTVXOBMASU-KKUMJFAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[(2S,4S,5S)-tetrahydro-4-hydroxy-5-hydroxymethyl-2-furanyl]-2-pentyn-1-yl t-butyldimethylsilyl ether 在 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 红铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 8.5h， 生成 (Z)-3-Chloro-5-((4aS,6S,7aS)-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxin-6-yl)-pent-2-en-1-ol
  参考文献：
  名称：

  Synthesis of ent-Haterumalide NA (ent-Oocydin A) Methyl Ester

  摘要：

  Stille coupling of allylic chloride 26 with vinylstannane 4a afforded 65% of 27 with the requisite skipped diene, vinyl chloride, and allylic oxygen functionality. Yamaguchi macrolactonization of 28 provided 65% of 29, which was elaborated to haterumalide NA methyl ester (32) by a Nozaki-Hiyama-Kishi coupling with 31.

  DOI：

  10.1021/ol0356789
• 作为产物：
  描述：

  5-[(2S,4S,5R)-tetrahydro-4-hydroxy-5-iodomethyl-2-furanyl]-2-pentyn-1-yl t-butyldimethylsilyl ether 在 吡啶 、 4-二甲氨基吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 5-[(2S,4S,5S)-tetrahydro-4-hydroxy-5-hydroxymethyl-2-furanyl]-2-pentyn-1-yl t-butyldimethylsilyl ether
  参考文献：
  名称：

  Synthesis of ent-Haterumalide NA (ent-Oocydin A) Methyl Ester

  摘要：

  Stille coupling of allylic chloride 26 with vinylstannane 4a afforded 65% of 27 with the requisite skipped diene, vinyl chloride, and allylic oxygen functionality. Yamaguchi macrolactonization of 28 provided 65% of 29, which was elaborated to haterumalide NA methyl ester (32) by a Nozaki-Hiyama-Kishi coupling with 31.

  DOI：

  10.1021/ol0356789

文献信息

• Synthesis of <i>ent</i>-Haterumalide NA (<i>ent</i>-Oocydin A) Methyl Ester
  作者：Yonghong Gu、Barry B. Snider

  DOI：10.1021/ol0356789

  日期：2003.11.1

  Stille coupling of allylic chloride 26 with vinylstannane 4a afforded 65% of 27 with the requisite skipped diene, vinyl chloride, and allylic oxygen functionality. Yamaguchi macrolactonization of 28 provided 65% of 29, which was elaborated to haterumalide NA methyl ester (32) by a Nozaki-Hiyama-Kishi coupling with 31.