(R)-2-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2-hydroxy-N,N-dimethyl-acetamide | 164215-25-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2-hydroxy-N,N-dimethyl-acetamide
• CAS: 164215-25-2
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: SUMQTBNINAIAAR-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-2-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2-hydroxy-N,N-dimethyl-acetamide 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 2 、 四丁基氟化铵 、 sodium hydride 、 potassium carbonate 、 戴斯-马丁氧化剂 、 臭氧 、 三乙胺 、 三苯基膦 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 374.01h， 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：

  3,3-dimethoxypentane 、 N,N-dimethyl-2,3,4-trihydroxybutyramide 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以90%的产率得到(R)-2-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2-hydroxy-N,N-dimethyl-acetamide
  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

文献信息

• Synthesis of (+)-Zaragozic Acid C
  作者：Erick M. Carreira、J. Du Bois

  DOI：10.1021/ja00102a074

  日期：1994.11