methyl (3R,5S)-3,5-dihydroxy-6-heptenoate | 629614-41-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (3R,5S)-3,5-dihydroxy-6-heptenoate
• 英文别名: methyl (3R,5S)-3,5-dihydroxyhept-6-enoate
• CAS: 629614-41-1
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: CWGIFURHYMAUMX-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 methyl (3R,5S)-3,5-dihydroxy-6-heptenoate 在 对甲苯磺酸 作用下， 反应 4.0h， 以95%的产率得到methyl (4R,6S)-6-ethenyl-2,2-dimethyl-1,3-dioxane-4-acetate
  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：

  6-[(2S)-2-hydroxybut-3-enyl]-2,2-dimethyl-1,3-dioxin-4-one 在 sodium tetrahydroborate 、 二乙基甲氧基硼烷 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 52.0h， 生成 methyl (3R,5S)-3,5-dihydroxy-6-heptenoate
  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

• Building blocks for skipped polyols: syn-1,3-acetonides by chemoenzymatic synthesis from cycloheptatriene
  作者：Mark A. Scialdone、Carl R. Johnson

  DOI：10.1016/0040-4039(94)02165-8

  日期：1995.1

  Enantiopure enones obtained via lipase asymmetrization of meso-diols derived from cycloheptatriene underwent tin-directed ring-openings to give syn-1,3-bis(silyloxy) olefins which were converted to their acetonides in a one-pot sequence.

  通过脂酶不对称化衍生自环庚三烯的内消旋二醇获得的对映体纯烯酮经过锡定向的开环，得到合成-1,3-双（甲硅烷氧基）烯烃，将其按一锅顺序转化为其丙酮化物。
• 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.