(2S,4R)-1-[tert-butyl(diphenyl)silyl]oxyhept-6-ene-2,4-diol | 153946-95-3

• 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: (2S,4R)-1-[tert-butyl(diphenyl)silyl]oxyhept-6-ene-2,4-diol
• CAS: 153946-95-3
• 化学式: C₂₃H₃₂O₃Si
• 分子量: 384.591
• InChiKey: NNGFOIWWYIPFHF-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4R)-1-[tert-butyl(diphenyl)silyl]oxyhept-6-ene-2,4-diol 在 吡啶 、 2,6-二甲基吡啶 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 22.83h， 生成 2,2-Dimethyl-propionic acid (2S,4R)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-hept-6-enyl ester
  参考文献：
  名称：

  A Synthesis of a C1-C7 Building Block for the Enantiomer of Hennoxazole A Utilizing a Regioselective Ring Opening of a Cyclic Acetal

  摘要：

  AC(1)-C-7 building block (4) for the enantiomer of hennoxazole A (1), an antivirus and analgesic active marine natural product, was efficiently synthesized from (S)-malic acid utilizing the following key steps: (1) the stereoselective construction of an anti-1,3-diol, (2) the regioselective ring opening of a cyclic acetal, and (3) the oxidative transformation of the olefin into the ketal of the methyl ketone in a one-pot process.

  DOI：

  10.3987/com-97-s(n)7
• 作为产物：
  描述：

  (S)-methyl 4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate 在 三甲基铝 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 溶剂黄146 、 乙腈 为溶剂， 反应 31.5h， 生成 (2S,4R)-1-[tert-butyl(diphenyl)silyl]oxyhept-6-ene-2,4-diol
  参考文献：
  名称：

  A Synthesis of a C1-C7 Building Block for the Enantiomer of Hennoxazole A Utilizing a Regioselective Ring Opening of a Cyclic Acetal

  摘要：

  AC(1)-C-7 building block (4) for the enantiomer of hennoxazole A (1), an antivirus and analgesic active marine natural product, was efficiently synthesized from (S)-malic acid utilizing the following key steps: (1) the stereoselective construction of an anti-1,3-diol, (2) the regioselective ring opening of a cyclic acetal, and (3) the oxidative transformation of the olefin into the ketal of the methyl ketone in a one-pot process.

  DOI：

  10.3987/com-97-s(n)7

文献信息

• Studies on the Stereochemistry of Theonezolides A-C: Elucidation of the Relative Configurations of 1,3-Diol Moieties of the C-4Å`C-17 Fragment
  作者：Jun'ichi Kobayashi、Makiko Yonezawa、Shinji Takeuchi、Masami Ishibashi

  DOI：10.3987/com-97-s6-1

  日期：——

  Four model compounds having syn and anti 1,3-diol type moieties corresponding to C-8/C-10 and C-14/C-16 positions contained in the C-4 similar to C-17 fragment of theonezolides A-C were prepared. Comparison of their spectral data suggested that the 1,3-diol at C-8/C-10 and the OH/OMe groups at C-14/C-16 positions of theonezolides A-C were both syn.
• A Synthesis of a C1-C7 Building Block for the Enantiomer of Hennoxazole A Utilizing a Regioselective Ring Opening of a Cyclic Acetal
  作者：Takayuki Shioiri、Nigel McFarlane、Yasumasa Hamada

  DOI：10.3987/com-97-s(n)7

  日期：——

  AC(1)-C-7 building block (4) for the enantiomer of hennoxazole A (1), an antivirus and analgesic active marine natural product, was efficiently synthesized from (S)-malic acid utilizing the following key steps: (1) the stereoselective construction of an anti-1,3-diol, (2) the regioselective ring opening of a cyclic acetal, and (3) the oxidative transformation of the olefin into the ketal of the methyl ketone in a one-pot process.