(2S,4R,6S,8R,9S)-4-Hydroxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-methanol | 137624-77-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4R,6S,8R,9S)-4-Hydroxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-methanol
• 英文别名: (2S,4R,6S,8R,9S)-2-(hydroxymethyl)-8,9-dimethyl-1,7-dioxaspiro[5.5]undecan-4-ol
• CAS: 137624-77-2
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: ICUYVBLLAFBLSH-KNZXXDILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  苯甲酰氯 、 (2S,4R,6S,8R,9S)-4-Hydroxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-methanol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以34%的产率得到(2S,4S,6S,8R,9S)-2-<(Benzoyloxy)methyl>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-4-ol
  参考文献：
  名称：

  Asymmetric synthesis of the milbemycin .beta.3 spiroketal subunit

  摘要：

  The milbemycin beta(3) spiroketal subunit 2 has been prepared with a high degree of enantiomeric purity. This represents the first reagent-controlled asymmetric synthesis of this complex molecule starting from an achiral starting material. Key reactions include Sharpless epoxidation, asymmetric hydroboration, and the Birch reduction of a meta-substituted cinnamyl epoxide. The enantiomeric excess of 2 was determined to be > 95% by a chiral shift H-1 NMR experiment with both optically active and racemic 2. The overall yield was 1.2% from methyl m-toluate (3).

  DOI：

  10.1021/jo00029a033
• 作为产物：
  描述：

  2-[(2R,5S,6R)-2-methoxy-5,6-dimethyloxan-2-yl]acetaldehyde 在 甲醇 、 1,3,4-trimethylimidazolidin-2-one 、 18-冠醚-6 、 Dowex W₅₀-1X 、 camphor-10-sulfonic acid 、 氨 、 氰化钾 、 lithium 、 lithium pyrrolidide 作用下， 生成 (2S,4R,6S,8R,9S)-4-Hydroxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-methanol
  参考文献：
  名称：

  米尔倍霉素β的螺缩醛片段的汇集合成1

  摘要：

  米尔倍霉素螺缩醛4，由（4制备小号，5 - [R）-4,5-二甲基戊-5-内酯5和（- [R）-1-（苄氧基甲基）环氧乙烷进行烷基化和中间螺缩醛氰醇的立体选择性还原脱氰7。

  DOI：

  10.1039/c39930000291

文献信息

• Convergent synthesis of the spiroacetal fragment of milbemycin β₁
  作者：Scott D. Rychnovsky、George Griesgraber

  DOI：10.1039/c39930000291

  日期：——

  Milbemycin spiroacetal 4 was prepared from (4S,5R)-4,5-dimethylpentan-5-olide 5 and (R)-1-(benzyloxymethyl)oxirane by alkylation and stereoselective reductive decyanation of the intermediate spiroacetal cyanohydrin 7.

  米尔倍霉素螺缩醛4，由（4制备小号，5 - [R）-4,5-二甲基戊-5-内酯5和（- [R）-1-（苄氧基甲基）环氧乙烷进行烷基化和中间螺缩醛氰醇的立体选择性还原脱氰7。
• Asymmetric synthesis of the milbemycin .beta.3 spiroketal subunit
  作者：Mark A. Holoboski、Emil Koft

  DOI：10.1021/jo00029a033

  日期：1992.1

  The milbemycin beta(3) spiroketal subunit 2 has been prepared with a high degree of enantiomeric purity. This represents the first reagent-controlled asymmetric synthesis of this complex molecule starting from an achiral starting material. Key reactions include Sharpless epoxidation, asymmetric hydroboration, and the Birch reduction of a meta-substituted cinnamyl epoxide. The enantiomeric excess of 2 was determined to be > 95% by a chiral shift H-1 NMR experiment with both optically active and racemic 2. The overall yield was 1.2% from methyl m-toluate (3).