(2S,4S)-1-[tert-butyl(diphenyl)silyl]oxyhept-6-ene-2,4-diol | 153947-03-6

• 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,4S)-1-[tert-butyl(diphenyl)silyl]oxyhept-6-ene-2,4-diol
• CAS: 153947-03-6
• 化学式: C₂₃H₃₂O₃Si
• 分子量: 384.591
• InChiKey: NNGFOIWWYIPFHF-PMACEKPBSA-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,4S)-1-[tert-butyl(diphenyl)silyl]oxyhept-6-ene-2,4-diol 在 sodium hydroxide 、 4-甲基苯磺酸吡啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 ((4S,6S)-6-allyl-2,2-dimethyl-1,3-dioxan-4-yl)methanol
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.3987/com-97-s6-1
• 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,4S)-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 stereochemistry of theonezolides A ∼ C: Determination of absolute stereochemistry of the C-4 ∼ C-17 fragment
  作者：Masaaki Sato、Shinji Takeuchi、Masami Ishibashi、Jun'ichi Kobayashi

  DOI：10.1016/s0040-4020(98)00190-2

  日期：1998.5

  The absolute stereochemistry of the C-4 ∼ C-17 fragment of theonezolides was establsihed as 8S, 10R, 14S, 16S on the basis of synthesis of the two diastereomers (4a and 4b) suggested from model studies and comparison of their spectral and optical data with those of natural specimen (4) obtained from ozonolysis of 1 ∼ 3.

  在模型研究和比较的基础上提出了两种非对映体（4a和4b）的合成基础上，酮内酯的C-4〜C-17片段的绝对立体化学被确立为8 S，10 R，14 S，16 S。它们的光谱和光学数据与臭氧分解1〜3获得的天然样品（4）的光谱和光学数据一致。
• 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.
• 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.