(S)-2-methoxy-4-methylpentanoic acid methyl ester | 912653-90-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-2-methoxy-4-methylpentanoic acid methyl ester
• 英文别名: methyl (2S)-2-methoxy-4-methylpentanoate
• CAS: 912653-90-8
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: MRITUNXBFHKLSY-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-methoxy-4-methylpentanoic acid methyl ester 在 sodium hypochlorite 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 molecular sieve 、 四丁基碘化铵 、 sodium hydride 、 碳酸氢钠 、 臭氧 、 potassium bromide 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.25h， 生成 (2S,3R,4S)-3-benzyloxy-4-methoxy-2,6-dimethylheptan-1-ol
  参考文献：
  名称：

  Stereoselective allyl transfer to chiral α-methoxycarbaldehydes: A model study related to the C-9/C-15 fragment of geldanamycin

  摘要：

  The enantiomerically pure alpha-methoxycarbaldehyde 3 was prepared from L-leucine in five steps and 31% overall yield. The aldehyde was subjected to a diastereoselective BF3-mediated crotylation with silane 4 and to various reagent-controlled addition reactions. The configuration of aldol addition products 19 and 20 was proven by single crystal X-ray crystallography. Based on these data spectral comparison allowed an unambiguous assignment of the desired anti,syn-crotylation product 2b and of the syn,syn-crotylation product 2a. Unexpectedly, product 2a of the BF3-mediated crotylation is formally the product of chelation-control. The anti, syn-crotylation product 2b, which is a model for the C-9/C-15 fragment of geldanamycin, was obtained by a reagent-controlled crotylation with the chiral (Z)-crotylborane 23. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.056
• 作为产物：
  描述：

  L-alpha-羟基异己酸 在 三甲基氯硅烷 、 sodium hydride 、 2,2-二甲氧基丙烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (S)-2-methoxy-4-methylpentanoic acid methyl ester
  参考文献：
  名称：

  Stereoselective allyl transfer to chiral α-methoxycarbaldehydes: A model study related to the C-9/C-15 fragment of geldanamycin

  摘要：

  The enantiomerically pure alpha-methoxycarbaldehyde 3 was prepared from L-leucine in five steps and 31% overall yield. The aldehyde was subjected to a diastereoselective BF3-mediated crotylation with silane 4 and to various reagent-controlled addition reactions. The configuration of aldol addition products 19 and 20 was proven by single crystal X-ray crystallography. Based on these data spectral comparison allowed an unambiguous assignment of the desired anti,syn-crotylation product 2b and of the syn,syn-crotylation product 2a. Unexpectedly, product 2a of the BF3-mediated crotylation is formally the product of chelation-control. The anti, syn-crotylation product 2b, which is a model for the C-9/C-15 fragment of geldanamycin, was obtained by a reagent-controlled crotylation with the chiral (Z)-crotylborane 23. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.056

文献信息

• [EN] PROSTACYCLIN DERIVATIVES<br/>[FR] DÉRIVÉS DE PROSTACYCLINE
  申请人：CONCERT PHARMACEUTICALS INC

  公开号：WO2011003058A1

  公开（公告）日：2011-01-06

  This invention relates to novel prostacyclin derivatives and acceptable salts thereof. The invention also provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions beneficially treated by prostacyclin, and in particular those diseases and conditions beneficially treated by dilators of systemic and pulmonary arterial vascular beds or by platelet aggregation inhibitors.

  本发明涉及新的前列腺素I2衍生物及其可接受的盐。该发明还提供了包含本发明化合物的组合物，以及将这些组合物用于治疗通过前列腺素I2有益治疗的疾病和状况的方法，特别是那些通过全身和肺动脉血管床扩张剂或通过血小板聚集抑制剂有益治疗的疾病和状况。
• Chin, E.; Goodby, J. W.; Patel, J. S., Molecular Crystals and Liquid Crystals (1969-1991), 1988, vol. 157, p. 163 - 192
  作者：Chin, E.、Goodby, J. W.、Patel, J. S.

  DOI：——

  日期：——
• Stereoselective allyl transfer to chiral α-methoxycarbaldehydes: A model study related to the C-9/C-15 fragment of geldanamycin
  作者：T HORNEFF、E HERDTWECK、S RANDOLL、T BACH

  DOI：10.1016/j.bmc.2006.05.056

  日期：2006.9.15

  The enantiomerically pure alpha-methoxycarbaldehyde 3 was prepared from L-leucine in five steps and 31% overall yield. The aldehyde was subjected to a diastereoselective BF3-mediated crotylation with silane 4 and to various reagent-controlled addition reactions. The configuration of aldol addition products 19 and 20 was proven by single crystal X-ray crystallography. Based on these data spectral comparison allowed an unambiguous assignment of the desired anti,syn-crotylation product 2b and of the syn,syn-crotylation product 2a. Unexpectedly, product 2a of the BF3-mediated crotylation is formally the product of chelation-control. The anti, syn-crotylation product 2b, which is a model for the C-9/C-15 fragment of geldanamycin, was obtained by a reagent-controlled crotylation with the chiral (Z)-crotylborane 23. (c) 2006 Elsevier Ltd. All rights reserved.