(2''S,4R,6R)-6-(2''-Benzyloxy-4''-pentenyl)-4-(methoxycarbonylmethyl)-2,2-dimethyl-1,3-dioxane | 251908-60-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2''S,4R,6R)-6-(2''-Benzyloxy-4''-pentenyl)-4-(methoxycarbonylmethyl)-2,2-dimethyl-1,3-dioxane
• 英文别名: methyl 2-[(4R,6R)-2,2-dimethyl-6-[(2S)-2-phenylmethoxypent-4-enyl]-1,3-dioxan-4-yl]acetate
• CAS: 251908-60-8
• 化学式: C₂₁H₃₀O₅
• 分子量: 362.466
• InChiKey: RBSNPFSLYYDODC-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2''S,4R,6R)-6-(2''-Benzyloxy-4''-pentenyl)-4-(methoxycarbonylmethyl)-2,2-dimethyl-1,3-dioxane 在 palladium on activated charcoal 伯吉斯试剂 、 三氟甲磺酸二丁硼 、 水 、 甲酸铵 、 4-甲基苯磺酸吡啶 、 臭氧 、 溶剂黄146 、 三乙胺 、 palladium dichloride 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 9.0h， 生成 {(4R,6R)-6-[(4S,6R)-6-((4R,6R)-6-{(4S,6S)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-methanol
  参考文献：
  名称：

  多烯大环内酯类抗生素 RK-397 多元醇部分的不对称合成

  摘要：

  利用新型多元醇合成方法，实现了新型多烯大环内酯抗生素 RK-397 的全功能多元醇部分的高度收敛和不对称合成。

  DOI：

  10.1055/s-2002-35584
• 作为产物：
  描述：

  Methyl (3S,5R,7S)-7-benzyloxy-3,5-bis(dimethylphenylsilyl)-9-decenoate 在 boron trifluoride diacetate 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 17.08h， 生成 (2''S,4R,6R)-6-(2''-Benzyloxy-4''-pentenyl)-4-(methoxycarbonylmethyl)-2,2-dimethyl-1,3-dioxane
  参考文献：
  名称：

  General and Asymmetric Synthesis of Protected 1,3,5-Triols with Pendant Functional Groups

  摘要：

  A stereoselective synthesis of enantiomerically purl 1,3,5-triols of any configuration has been developed. These triols carry suitable functional groups at the termini of the chain which should allow for easy and efficient coupling of two building blocks. The silyloxy-Cope rearrangement of syn-aldols was used to prepare a common advanced intermediate for the synthesis of all four stereoisomeric triols. Three synthetic operations-an allylboration, an oxidative desilylation, and a conjugate addition reaction-were employed to assemble the target molecules. Their terminal double bond may either be cleaved to give the corresponding aldehydes or oxidized to the methyl ketones in a Wacker process to provide access to two subunits for a coupling reaction.

  DOI：

  10.1002/(sici)1521-3765(19991001)5:10<2850::aid-chem2850>3.0.co;2-7

文献信息

• General and Asymmetric Synthesis of Protected 1,3,5-Triols with Pendant Functional Groups
  作者：Christoph Schneider、Markus Rehfeuter

  DOI：10.1002/(sici)1521-3765(19991001)5:10<2850::aid-chem2850>3.0.co;2-7

  日期：1999.10.1

  A stereoselective synthesis of enantiomerically purl 1,3,5-triols of any configuration has been developed. These triols carry suitable functional groups at the termini of the chain which should allow for easy and efficient coupling of two building blocks. The silyloxy-Cope rearrangement of syn-aldols was used to prepare a common advanced intermediate for the synthesis of all four stereoisomeric triols. Three synthetic operations-an allylboration, an oxidative desilylation, and a conjugate addition reaction-were employed to assemble the target molecules. Their terminal double bond may either be cleaved to give the corresponding aldehydes or oxidized to the methyl ketones in a Wacker process to provide access to two subunits for a coupling reaction.
• Asymmetric Synthesis of the Polyol Portion of the Polyene Macrolide Antibiotic RK-397
  作者：Christoph Schneider、Frank Tolksdorf、Markus Rehfeuter

  DOI：10.1055/s-2002-35584

  日期：——

  A highly convergent and asymmetric synthesis of a fully functionalized polyol portion of the new polyene macrolide antibiotic RK-397 has been achieved taking advantage of a novel polyol synthesis.

  利用新型多元醇合成方法，实现了新型多烯大环内酯抗生素 RK-397 的全功能多元醇部分的高度收敛和不对称合成。