(2R,3S)-5-Methyl-2,3-dihydroxyhexanoate ethyl ester | 181025-89-8

• 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: (2R,3S)-5-Methyl-2,3-dihydroxyhexanoate ethyl ester
• 英文别名: ethyl (2R,3S)-2,3-dihydroxy-5-methylhexanoate
• CAS: 181025-89-8
• 化学式: C₉H₁₈O₄
• 分子量: 190.24
• InChiKey: HARPHDPYHGCREO-JGVFFNPUSA-N

物化性质

• 沸点：
  293.0±7.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (2R,3S)-5-Methyl-2,3-dihydroxyhexanoate ethyl ester 在 palladium on activated charcoal 咪唑 、 lithium hydroxide 、 sodium azide 、 氢氟酸 、 氢气 、 silver(I) acetate 、 氯甲酸乙酯 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 253.5h， 生成 (3S,4S)-(-)-他汀
  参考文献：
  名称：

  Unusual Regioselection in the Mitsunobu Reactions of syn-2,3-Dihydroxy Esters:  Synthesis of Statine and Its Diastereomer

  摘要：

  Mitsunobu reactions of syn-2,3-dihydroxy esters exhibit a complete regioselection for the beta-hydroxyl group. Benzoylation, azidation, and tosylation have been performed under these conditions. beta-Functionalizations of syn-2,3-dihydroxy esters are uncommon, and the Mitsunobu reactions are complementary to other diol chemistries in the regioselection. In addition, the configurational inversion accompanying the Mitsunobu protocol offers a means for diastereochemical diversity, as exemplified by a synthesis of statine and its anti diastereomer. These findings will further expand the synthetic utilities of the Sharpless AD process.

  DOI：

  10.1021/jo015967f
• 作为产物：
  描述：

  5-甲基己基-2-丁烯酸乙酯 在 AD-mix-α 、 甲基磺酰胺 作用下， 以 水 、 叔丁醇 为溶剂， 反应 19.0h， 以96%的产率得到(2R,3S)-5-Methyl-2,3-dihydroxyhexanoate ethyl ester
  参考文献：
  名称：

  Unusual Regioselection in the Mitsunobu Reactions of syn-2,3-Dihydroxy Esters:  Synthesis of Statine and Its Diastereomer

  摘要：

  Mitsunobu reactions of syn-2,3-dihydroxy esters exhibit a complete regioselection for the beta-hydroxyl group. Benzoylation, azidation, and tosylation have been performed under these conditions. beta-Functionalizations of syn-2,3-dihydroxy esters are uncommon, and the Mitsunobu reactions are complementary to other diol chemistries in the regioselection. In addition, the configurational inversion accompanying the Mitsunobu protocol offers a means for diastereochemical diversity, as exemplified by a synthesis of statine and its anti diastereomer. These findings will further expand the synthetic utilities of the Sharpless AD process.

  DOI：

  10.1021/jo015967f

文献信息

• Asymmetric synthesis of the Abbott amino dihydroxyethylene dipeptide isostere subunit
  作者：Mansour Haddad、Marc Larchevêque

  DOI：10.1016/0040-4039(96)00874-x

  日期：1996.6

  The aminodiol 1b, a N-benzyl protected form of the Abbott dipeptide isostere la is prepared, starling from an appropriate alpha,beta-unsaturated ester, involving an asymmetric dihydroxylation and a rearrangement of an intermediate anti alpha,beta-aminoepoxide. Copyright (C) 1996 Published by Elsevier Science Ltd
• Unusual Regioselection in the Mitsunobu Reactions of <i>s</i><i>yn</i>-2,3-Dihydroxy Esters:  Synthesis of Statine and Its Diastereomer
  作者：Soo Y. Ko

  DOI：10.1021/jo015967f

  日期：2002.4.1

  Mitsunobu reactions of syn-2,3-dihydroxy esters exhibit a complete regioselection for the beta-hydroxyl group. Benzoylation, azidation, and tosylation have been performed under these conditions. beta-Functionalizations of syn-2,3-dihydroxy esters are uncommon, and the Mitsunobu reactions are complementary to other diol chemistries in the regioselection. In addition, the configurational inversion accompanying the Mitsunobu protocol offers a means for diastereochemical diversity, as exemplified by a synthesis of statine and its anti diastereomer. These findings will further expand the synthetic utilities of the Sharpless AD process.