(S)-4-(t-butyldiphenylsiloxy)-2-(triethylsiloxy)butanal | 479092-55-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (S)-4-(t-butyldiphenylsiloxy)-2-(triethylsiloxy)butanal
• 英文别名: (S)-4-(tert-butyldiphenylsilyloxy)-2-triethylsiloxybutanal；(2S)-4-[tert-butyl(diphenyl)silyl]oxy-2-triethylsilyloxybutanal
• CAS: 479092-55-2
• 化学式: C₂₆H₄₀O₃Si₂
• 分子量: 456.773
• InChiKey: HTPYOQOANZDCBX-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-(t-butyldiphenylsiloxy)-2-(triethylsiloxy)butanal 在 正丁基锂 、 ditrityl peroxide 、 ethylenediamine Tetraacetic Acid 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 4.0h， 生成 (12R,13S,14S)-(3E,5E,7E,9E,12E)-16-(tert-butyldiphenylsiloxy)-12-cyano-2-[(E)-ethylidene]-4,10-dimethyl-11-oxo-14-triethylsiloxy-12,13-epoxyhexadeca-3,5,7,9-tetraenoic acid methyl ester
  参考文献：
  名称：

  The diastereoselective asymmetric total synthesis of NG-391, a neuronal cell-protecting molecule

  摘要：

  The stereocontrolled total synthesis of (+)-NG-391, a neuronal cell-protecting molecule, is described along with the determination of its absolute stereochemistry. The following reactions in this synthesis are particularly noteworthy: (1) The stereoselective construction of the conjugated (E,E,E,E,E)-pentaene from an (E,E,E)-alcohol using an IBX oxidation followed by stereoselective Horner-Emmons reaction. (2) The (E)-selective Knoevenagel condensation of a beta-ketonitrile with a chiral 2-alkoxyaldehyde prepared from (S)-malic acid. (3) A diastereoselective epoxidation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01290-5
• 作为产物：
  描述：

  Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate 在 咪唑 、 pyridine-SO3 complex 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (S)-4-(t-butyldiphenylsiloxy)-2-(triethylsiloxy)butanal
  参考文献：
  名称：

  The diastereoselective asymmetric total synthesis of NG-391, a neuronal cell-protecting molecule

  摘要：

  The stereocontrolled total synthesis of (+)-NG-391, a neuronal cell-protecting molecule, is described along with the determination of its absolute stereochemistry. The following reactions in this synthesis are particularly noteworthy: (1) The stereoselective construction of the conjugated (E,E,E,E,E)-pentaene from an (E,E,E)-alcohol using an IBX oxidation followed by stereoselective Horner-Emmons reaction. (2) The (E)-selective Knoevenagel condensation of a beta-ketonitrile with a chiral 2-alkoxyaldehyde prepared from (S)-malic acid. (3) A diastereoselective epoxidation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01290-5

文献信息

• An acid-catalyzed ring-switch reaction of lactams to lactones: concise synthesis of 2,4-dialkyl-3-hydroxybutanolides
  作者：Chiaki Yamauchi、Masami Kuriyama、Rumiko Shimazawa、Tsumoru Morimoto、Kiyomi Kakiuchi、Ryuichi Shirai

  DOI：10.1016/j.tet.2008.01.107

  日期：2008.3

  A novel approach for the synthesis of 2,4-dialkyl-3-hydroxybutanolides, having three successive stereogenic centers, by an acid-catalyzed ring-switch reaction of 2-(2-hydroxyalkyl)lactams is described. This transformation was applied to the synthesis of the key intermediates of teromerase inhibitor UCS1025A. (c) 2008 Elsevier Ltd. All rights reserved.
• [EN] NOVEL BIOACTIVE SUBSTANCE EXHIBITING ANTIMALARIAL ACTIVITY, AND USE FOR SAME<br/>[FR] NOUVELLE SUBSTANCE BIOACTIVE PRÉSENTANT UNE ACTIVITÉ ANTIPALUDIQUE ET SON UTILISATION<br/>[JA] 抗マラリア活性を示す新規生理活性物質及びその用途
  申请人：[en]RIKEN;[ja]国立研究開発法人理化学研究所

  公开号：WO2022186328A1

  公开（公告）日：2022-09-09

  本発明は、次式（Ｉ）： で示される化合物、及び前記化合物を含有する抗マラリア薬に関する。
• The diastereoselective asymmetric total synthesis of NG-391, a neuronal cell-protecting molecule
  作者：Yujiro Hayashi、Junichiro Yamaguchi、Mitsuru Shoji

  DOI：10.1016/s0040-4020(02)01290-5

  日期：2002.12

  The stereocontrolled total synthesis of (+)-NG-391, a neuronal cell-protecting molecule, is described along with the determination of its absolute stereochemistry. The following reactions in this synthesis are particularly noteworthy: (1) The stereoselective construction of the conjugated (E,E,E,E,E)-pentaene from an (E,E,E)-alcohol using an IBX oxidation followed by stereoselective Horner-Emmons reaction. (2) The (E)-selective Knoevenagel condensation of a beta-ketonitrile with a chiral 2-alkoxyaldehyde prepared from (S)-malic acid. (3) A diastereoselective epoxidation. (C) 2002 Elsevier Science Ltd. All rights reserved.