(2S,3S,4S,6S)-6-[(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-1-hydroxy-ethyl)-but-3-ynyloxy]-2-methyl-tetrahydro-pyran-3,4-diol | 476469-60-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2S,3S,4S,6S)-6-[(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-1-hydroxy-ethyl)-but-3-ynyloxy]-2-methyl-tetrahydro-pyran-3,4-diol
• 英文别名: (2S,3S,4S,6S)-6-[(2S,3R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-2-hydroxyhex-5-yn-3-yl]oxy-2-methyloxane-3,4-diol
• CAS: 476469-60-0
• 化学式: C₁₈H₃₄O₆Si
• 分子量: 374.55
• InChiKey: VDJYCPLTWOIXOT-OGEQHFGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,6S)-6-[(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-1-hydroxy-ethyl)-but-3-ynyloxy]-2-methyl-tetrahydro-pyran-3,4-diol 在 六羰基钨 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 41.0h， 生成 4-Nitro-benzoic acid (1S,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-[(2S,4S,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-5-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-1-methyl-pent-4-ynyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of l-Oliose Trisaccharide via Iterative Alkynol Cycloisomerization and Acid-Catalyzed Glycosylation

  摘要：

  [GRAPHICS]The synthesis of an all-alpha L-Oliose diastereomer of digitoxin provides valuable insights into the generality and protective-group dependence of acid-catalyzed glycosylations of glycals to 2-deoxycarbohydrates.

  DOI：

  10.1021/ol026886o
• 作为产物：
  描述：

  4-Nitro-benzoic acid (1S,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-1-methyl-pent-4-ynyl ester 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到(2S,3S,4S,6S)-6-[(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-1-hydroxy-ethyl)-but-3-ynyloxy]-2-methyl-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  Stereoselective Synthesis of l-Oliose Trisaccharide via Iterative Alkynol Cycloisomerization and Acid-Catalyzed Glycosylation

  摘要：

  [GRAPHICS]The synthesis of an all-alpha L-Oliose diastereomer of digitoxin provides valuable insights into the generality and protective-group dependence of acid-catalyzed glycosylations of glycals to 2-deoxycarbohydrates.

  DOI：

  10.1021/ol026886o