6-(4-benzyloxy-2-hydroxybutyl)-tetrahydropyran-2-one | 500208-46-8

• 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: 6-(4-benzyloxy-2-hydroxybutyl)-tetrahydropyran-2-one
• 英文别名: (6S)-6-[(2S)-2-hydroxy-4-phenylmethoxybutyl]oxan-2-one
• CAS: 500208-46-8
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: CSWCXXDREIEUGJ-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(4-benzyloxy-2-hydroxybutyl)-tetrahydropyran-2-one 在 咪唑 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 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-苄氧基-2-丁酮 在 RuCl₂[(S)-BINAP] 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 、 甲苯 为溶剂， -78.0~30.0 ℃ 、9.5 MPa 条件下， 反应 90.2h， 生成 6-(4-benzyloxy-2-hydroxybutyl)-tetrahydropyran-2-one
  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

• BRYOSTATIN ANALOGUES, SYNTHETIC METHODS AND USES
  申请人：Wender Paul A.

  公开号：US20100280262A1

  公开（公告）日：2010-11-04

  Biologically active compounds related to the bryostatin family of compounds, having simplified spacer domains and/or improved recognition domains are disclosed, including methods of preparing and utilizing the same.
• Bryostatin Analogues, Synthetic Methods and Uses
  申请人：The Board of Trustees of the Leland Stanford Juni

  公开号：US20130123518A1

  公开（公告）日：2013-05-16

  Biologically active compounds related to the bryostatin family of compounds, having simplified spacer domains and/or improved recognition domains are disclosed, including methods of preparing and utilizing the same.
• US8735609B2
  申请人：——

  公开号：US8735609B2

  公开（公告）日：2014-05-27
• 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.