(2S,3S,4S,6S)-6-{(2S,3R,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(1R,2S)-2-(tert-butyl-dimethyl-silanyloxy)-1-((S)-1-hydroxy-ethyl)-but-3-ynyloxy]-2-methyl-tetrahydro-pyran-3-yloxy}-2-methyl-tetrahydro-pyran-3,4-diol | 476469-63-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,6S)-6-{(2S,3R,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(1R,2S)-2-(tert-butyl-dimethyl-silanyloxy)-1-((S)-1-hydroxy-ethyl)-but-3-ynyloxy]-2-methyl-tetrahydro-pyran-3-yloxy}-2-methyl-tetrahydro-pyran-3,4-diol
• 英文别名: (2S,3S,4S,6S)-6-[(2S,3R,4S,6S)-4-[tert-butyl(dimethyl)silyl]oxy-6-[(2S,3R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-2-hydroxyhex-5-yn-3-yl]oxy-2-methyloxan-3-yl]oxy-2-methyloxane-3,4-diol
• CAS: 476469-63-3
• 化学式: C₃₀H₅₈O₉Si₂
• 分子量: 618.956
• InChiKey: BLTFBVWAZFGIKE-GZVFPVECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,6S)-6-{(2S,3R,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(1R,2S)-2-(tert-butyl-dimethyl-silanyloxy)-1-((S)-1-hydroxy-ethyl)-but-3-ynyloxy]-2-methyl-tetrahydro-pyran-3-yloxy}-2-methyl-tetrahydro-pyran-3,4-diol 在 六羰基钨 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 Acetic acid (2S,3R,4S,6S)-3-acetoxy-6-{(2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(2S,3R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3-yloxy}-2-methyl-tetrahydro-pyran-4-yl 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：

  (3S,4R,5S)-1-(trimethylsilyl)-4,5-epoxyhex-1-yn-3-ol 在 咪唑 、 camphor-10-sulfonic acid 、 二异丁基氢化铝 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 40.0h， 生成 (2S,3S,4S,6S)-6-{(2S,3R,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(1R,2S)-2-(tert-butyl-dimethyl-silanyloxy)-1-((S)-1-hydroxy-ethyl)-but-3-ynyloxy]-2-methyl-tetrahydro-pyran-3-yloxy}-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

文献信息

• Stereoselective Synthesis of <scp>l</scp>-Oliose Trisaccharide via Iterative Alkynol Cycloisomerization and Acid-Catalyzed Glycosylation
  作者：Frank E. McDonald、Minglang Wu

  DOI：10.1021/ol026886o

  日期：2002.10.1

  [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.