(2R,3S,4S)-4-methoxy-2,6-dimethylheptane-1,3-diol | 912653-94-2

• 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: (2R,3S,4S)-4-methoxy-2,6-dimethylheptane-1,3-diol
• CAS: 912653-94-2
• 化学式: C₁₀H₂₂O₃
• 分子量: 190.283
• InChiKey: CECCRBYBNGGGNS-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-4-methoxy-2,6-dimethylheptane-1,3-diol 、 苯甲醛 在 三氟乙酸 、 原甲酸三甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以68%的产率得到(2S,4S,5R)-4-((S)-1-methoxy-3-methylbutyl)-5-methyl-2-phenyl-[1,3]dioxane
  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 sodium hypochlorite 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三甲基氯硅烷 、 三氟甲磺酸二丁硼 、 sodium hydride 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 2,2-二甲氧基丙烷 、 potassium bromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.5h， 生成 (2R,3S,4S)-4-methoxy-2,6-dimethylheptane-1,3-diol
  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