(2R,3R)-7-Benzyloxy-2-methyl-heptane-1,3-diol | 171189-81-4

• 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,3R)-7-Benzyloxy-2-methyl-heptane-1,3-diol
• CAS: 171189-81-4
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: XCKWTINERZQPLA-UKRRQHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  18.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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,3R)-7-Benzyloxy-2-methyl-heptane-1,3-diol 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 正丁基锂 、 草酰氯 、 2 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 戴斯-马丁氧化剂 、 二甲基亚砜 、 苯基锂 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 环己烷 、 水 、 乙酸乙酯 为溶剂， -78.0~65.0 ℃ 、101.33 kPa 条件下， 反应 416.84h， 生成 2,2-Dimethyl-propionic acid (E)-(R)-7-{(S)-4-[(R)-benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-2-oxo-[1,3]dioxolan-4-yl}-1-((R)-1-methyl-2-phenyl-ethyl)-5-oxo-hept-6-enyl ester
  参考文献：
  名称：

  (+)-Zaragozic Acid C: Synthesis and Related Studies

  摘要：

  The asymmetric synthesis of the potent squalene synthase inhibitor (+)-zaragozic acid C is described. The synthesis allows for the preparation of multigram quantities of the dioxabicyclooctane core common to all members of this class of fungal metabolites. Supporting studies include (1) the use of [Cr(OAc)(2) . H2O](2) for the stereoselective reduction of ynones to trans enones, (2) an investigation of the diastereoselective dihydroxylation of gamma-alkoxy-alpha,beta-trans trans enones, and (3) nucleophilic addition of Me(3)SiC equivalent to CLi to a dioxabicyclooctanone, wherein the product diastereoselectivity is observed to vary as a function of cosolvents (tertiary amines) and additives (LiBr). In addition, an acylation protocol is reported which permits the regioselective installation of the C(6) O-acyl side chain.

  DOI：

  10.1021/ja00136a008
• 作为产物：
  描述：

  (2S,3R)-7-Benzyloxy-3-hydroxy-2-methyl-heptanoic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以92%的产率得到(2R,3R)-7-Benzyloxy-2-methyl-heptane-1,3-diol
  参考文献：
  名称：

  (+)-Zaragozic Acid C: Synthesis and Related Studies

  摘要：

  The asymmetric synthesis of the potent squalene synthase inhibitor (+)-zaragozic acid C is described. The synthesis allows for the preparation of multigram quantities of the dioxabicyclooctane core common to all members of this class of fungal metabolites. Supporting studies include (1) the use of [Cr(OAc)(2) . H2O](2) for the stereoselective reduction of ynones to trans enones, (2) an investigation of the diastereoselective dihydroxylation of gamma-alkoxy-alpha,beta-trans trans enones, and (3) nucleophilic addition of Me(3)SiC equivalent to CLi to a dioxabicyclooctanone, wherein the product diastereoselectivity is observed to vary as a function of cosolvents (tertiary amines) and additives (LiBr). In addition, an acylation protocol is reported which permits the regioselective installation of the C(6) O-acyl side chain.

  DOI：

  10.1021/ja00136a008