(2S,3S,4S)-(-)-1-(tert-butyldimethylsilyloxy)-2,4-dimethyl-6-trimethylsilyl-5-hexyn-3-ol | 540473-46-9

• 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,3S,4S)-(-)-1-(tert-butyldimethylsilyloxy)-2,4-dimethyl-6-trimethylsilyl-5-hexyn-3-ol
• CAS: 540473-46-9
• 化学式: C₁₇H₃₆O₂Si₂
• 分子量: 328.643
• InChiKey: NFTKOYRXDGRBSA-JYJNAYRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-(-)-1-(tert-butyldimethylsilyloxy)-2,4-dimethyl-6-trimethylsilyl-5-hexyn-3-ol 在 2,6-二甲基吡啶 、 4-甲基苯磺酸吡啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (2S,3S,4S)-(+)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-6-trimethylsilyl-5-hexyn-1-ol
  参考文献：
  名称：

  Total Synthesis of (−)- and (+)-Membrenone C

  摘要：

  [GRAPHICS]A synthesis of the polypropionate marine defense substance (+)-membrenone C and its enantiomer that starts from (S)-2-methyl-3-(tert-butyldimethylsilyloxy)propanal is described. Key steps include (1) additions of chiral allenylmetal reagents to effect both chain homologation and the concomitant introduction of four stereo centers, (2) a bis-intramolecular hydrosilylation-oxidation sequence to install beta-hydroxy ketone subunits, and (3) a bis-intramolecular aldol reaction to construct the two dihydropyrone termini.

  DOI：

  10.1021/ol034367v
• 作为产物：
  描述：

  (2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal 、 (S)-4-trimethylsilyl-3-butyn-2-yl mesylate 在 palladium diacetate indium iodide 、 三苯基膦 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 2.0h， 以75%的产率得到(2S,3S,4S)-(-)-1-(tert-butyldimethylsilyloxy)-2,4-dimethyl-6-trimethylsilyl-5-hexyn-3-ol
  参考文献：
  名称：

  Total Synthesis of (−)- and (+)-Membrenone C

  摘要：

  [GRAPHICS]A synthesis of the polypropionate marine defense substance (+)-membrenone C and its enantiomer that starts from (S)-2-methyl-3-(tert-butyldimethylsilyloxy)propanal is described. Key steps include (1) additions of chiral allenylmetal reagents to effect both chain homologation and the concomitant introduction of four stereo centers, (2) a bis-intramolecular hydrosilylation-oxidation sequence to install beta-hydroxy ketone subunits, and (3) a bis-intramolecular aldol reaction to construct the two dihydropyrone termini.

  DOI：

  10.1021/ol034367v