Ethyl (2S,3S,5S)-3-hydroxy-5,6-(isopropylidenedioxy)-2-methylhexanoate | 139631-13-3

• 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: Ethyl (2S,3S,5S)-3-hydroxy-5,6-(isopropylidenedioxy)-2-methylhexanoate
• 英文别名: ethyl (2S,3S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2-methylbutanoate
• CAS: 139631-13-3
• 化学式: C₁₂H₂₂O₅
• 分子量: 246.304
• InChiKey: NPZCLCMGWPRHCD-GUBZILKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Ethyl (2S,3S,5S)-3-hydroxy-5,6-(isopropylidenedioxy)-2-methylhexanoate 在 咪唑 、 4-二甲氨基吡啶 、 正丁基锂 、 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 59.5h， 生成 Methyl (1R(1'E,3'E,5'E),2S,3S,5S)-3-O-(tert-butyldiphenylsilyl)-1-(1',5'-dimethyl-6'-(2-methyloxazol-4-yl)-1',3',5'-hexatrienyl)-2-methyl-2,4-dideoxymannopyranoside
  参考文献：
  名称：

  Synthesis of the lower subunit of rhizoxin

  摘要：

  Full details of a study leading to a synthesis of the optically active C13-C26 lower subunit of rhizoxin including the side-chain chromophore characteristic of the full class of antimitotic agents are described. A key element of the synthesis is the stereoselective introduction of the C18-C19 trisubstituted olefin through use of a Wadsworth-Horner-Emmons condensation of 3 with beta-keto phosphonate 38 bearing resident functionality suitable for the diastereoselective introduction of C15-C17 employing a hydroxyl-directed reduction of the resultant beta-hydroxy ketone.

  DOI：

  10.1021/jo00034a010
• 作为产物：
  描述：

  (3'S,5'S,4R,5S)-3-(3'-Hydroxy-5',6'-(isopropylidenedioxy)hexanoyl)-4-methyl-5-phenyl-2-oxazolidinone 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 39.17h， 生成 Ethyl (2S,3S,5S)-3-hydroxy-5,6-(isopropylidenedioxy)-2-methylhexanoate
  参考文献：
  名称：

  Synthesis of the lower subunit of rhizoxin

  摘要：

  Full details of a study leading to a synthesis of the optically active C13-C26 lower subunit of rhizoxin including the side-chain chromophore characteristic of the full class of antimitotic agents are described. A key element of the synthesis is the stereoselective introduction of the C18-C19 trisubstituted olefin through use of a Wadsworth-Horner-Emmons condensation of 3 with beta-keto phosphonate 38 bearing resident functionality suitable for the diastereoselective introduction of C15-C17 employing a hydroxyl-directed reduction of the resultant beta-hydroxy ketone.

  DOI：

  10.1021/jo00034a010

文献信息

• Synthesis of the lower subunit of rhizoxin
  作者：Dale L. Boger、Timothy T. Curran

  DOI：10.1021/jo00034a010

  日期：1992.4

  Full details of a study leading to a synthesis of the optically active C13-C26 lower subunit of rhizoxin including the side-chain chromophore characteristic of the full class of antimitotic agents are described. A key element of the synthesis is the stereoselective introduction of the C18-C19 trisubstituted olefin through use of a Wadsworth-Horner-Emmons condensation of 3 with beta-keto phosphonate 38 bearing resident functionality suitable for the diastereoselective introduction of C15-C17 employing a hydroxyl-directed reduction of the resultant beta-hydroxy ketone.