9-benzyloxy-5,7-dioxononanoic acid methyl ester | 500208-44-6

• 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: 9-benzyloxy-5,7-dioxononanoic acid methyl ester
• 英文别名: Methyl 5,7-dioxo-9-phenylmethoxynonanoate
• CAS: 500208-44-6
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: KIFOWJSENICSAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-benzyloxy-5,7-dioxononanoic acid methyl ester 在 RuCl₂[(S)-BINAP] 咪唑 、 正丁基锂 、 氢气 、 silica gel 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -78.0~30.0 ℃ 、9.5 MPa 条件下， 反应 99.0h， 生成 4-{6-[4-benzyloxy-2-(tert-butyldiphenylsilanyloxy)-butyl]-2-hydroxytetrahydropyran-2-yl}-3-oxobutyric acid ethyl ester
  参考文献：
  名称：

  A Concise, Selective Synthesis of the Polyketide Spacer Domain of a Potent Bryostatin Analogue

  摘要：

  [GRAPHICS]A concise, asymmetric synthesis of the polyketide spacer domain portion (C1-C13) of a highly potent bryostatin analogue was developed. The route utilizes asymmetric hydrogenation methodology to install the C3, C5, and C11 stereocenters, while a substrate directed syn reduction sets the C9 stereocenter. The spacer domain 1 is obtained in 10 steps with a 25% overall yield and is readily incorporated into the synthesis of 2.

  DOI：

  10.1021/ol0272390
• 作为产物：
  描述：

  4-氯甲酰基丁酸甲酯 、 4-苄氧基-2-丁酮 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.2h， 以68%的产率得到9-benzyloxy-5,7-dioxononanoic acid methyl ester
  参考文献：
  名称：

  A Concise, Selective Synthesis of the Polyketide Spacer Domain of a Potent Bryostatin Analogue

  摘要：

  [GRAPHICS]A concise, asymmetric synthesis of the polyketide spacer domain portion (C1-C13) of a highly potent bryostatin analogue was developed. The route utilizes asymmetric hydrogenation methodology to install the C3, C5, and C11 stereocenters, while a substrate directed syn reduction sets the C9 stereocenter. The spacer domain 1 is obtained in 10 steps with a 25% overall yield and is readily incorporated into the synthesis of 2.

  DOI：

  10.1021/ol0272390

文献信息

• A Concise, Selective Synthesis of the Polyketide Spacer Domain of a Potent Bryostatin Analogue
  作者：Paul A. Wender、Alexander V. W. Mayweg、Christopher L. VanDeusen

  DOI：10.1021/ol0272390

  日期：2003.2.1

  [GRAPHICS]A concise, asymmetric synthesis of the polyketide spacer domain portion (C1-C13) of a highly potent bryostatin analogue was developed. The route utilizes asymmetric hydrogenation methodology to install the C3, C5, and C11 stereocenters, while a substrate directed syn reduction sets the C9 stereocenter. The spacer domain 1 is obtained in 10 steps with a 25% overall yield and is readily incorporated into the synthesis of 2.