(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-ethylbutanal

• 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)-3-(tert-butyldimethylsilyloxy)-2-ethylbutanal
• 英文别名: (2S,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-ethylbutanal
• 化学式: C₁₂H₂₆O₂Si
• 分子量: 230.423
• InChiKey: ZHGPASCTXASFDG-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-ethylbutanal 、 乙烯基氯化镁 以 乙醚 为溶剂， 以98%的产率得到(4R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-4-ethylhex-1-en-3-ol
  参考文献：
  名称：

  Synthesis of the glycosyl lactol moiety of halichoblelide

  摘要：

  The enantioselective synthesis of the 2-deoxy-alpha-L-fucosyl lactol moiety of halichoblelide, a potent cytotoxin isolated from an actinomycete of marine origin, was achieved using a diastereoselective addition of a dithianyl anion to a chiral aldehyde intermediate and a stereoselective glycosidation of a hydroxy lactone intermediate derived from the addition product with a protected L-fucal as the key steps. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.100

文献信息

• Synthesis of the glycosyl lactol moiety of halichoblelide
  作者：Yohsuke Satoh、Takashi Nakahata、Shigefumi Kuwahara

  DOI：10.1016/j.tet.2007.08.100

  日期：2007.11

  The enantioselective synthesis of the 2-deoxy-alpha-L-fucosyl lactol moiety of halichoblelide, a potent cytotoxin isolated from an actinomycete of marine origin, was achieved using a diastereoselective addition of a dithianyl anion to a chiral aldehyde intermediate and a stereoselective glycosidation of a hydroxy lactone intermediate derived from the addition product with a protected L-fucal as the key steps. (c) 2007 Elsevier Ltd. All rights reserved.