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 | 171189-93-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 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
• CAS: 171189-93-8
• 化学式: C₃₉H₅₂O₉
• 分子量: 664.836
• InChiKey: KDQHOHNZYTZOTI-KQSMUJNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.54
• 重原子数：
  48.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  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 在 四氧化锇 、 甲基磺酰胺 、 N-甲基吗啉氧化物 作用下， 以 丙酮 、 叔丁醇 为溶剂， 反应 18.0h， 以5 mg的产率得到2,2-Dimethyl-propionic acid (1R,6S,7S)-7-{(R)-4-[(R)-benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-2-oxo-[1,3]dioxolan-4-yl}-6,7-dihydroxy-1-((R)-1-methyl-2-phenyl-ethyl)-5-oxo-heptyl 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：

  2,2-Dimethyl-propionic acid (R)-5-hydroxy-1-((R)-1-methyl-2-phenyl-ethyl)-pentyl ester 在 吡啶 、 正丁基锂 、 草酰氯 、 2 、 四丁基氟化铵 、 戴斯-马丁氧化剂 、 二甲基亚砜 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 345.34h， 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