allenyl 2-deoxy-3,4,6-tri-O-t-butyldimethylsilyl-β-D-galactopyranoside | 940933-74-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allenyl 2-deoxy-3,4,6-tri-O-t-butyldimethylsilyl-β-D-galactopyranoside
• CAS: 940933-74-4
• 化学式: C₂₇H₅₆O₅Si₃
• 分子量: 544.995
• InChiKey: BOKFEBHFHABIPC-MOUTVQLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.22
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allenyl 2-deoxy-3,4,6-tri-O-t-butyldimethylsilyl-β-D-galactopyranoside 、 (cyclohex-1-enyl)(morpholin-4-yl)methanone 在 正丁基锂 、 1,10-菲罗啉 、 lithium chloride 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.78h， 以93%的产率得到3-hydroxy-1-methylene-1,4,5,6,7,7a-hexahydroinden-2-one
  参考文献：
  名称：

  Traceless Chiral Auxiliaries for the Allene Ether Nazarov Cyclization

  摘要：

  The key stereochemical factors that determine transfer of asymmetry from the chiral auxiliary to the cyclopentenone in the allene ether version of the Nazarov reaction have been elucidated. On the basis of the new insights into the mechanism, two highly effective chiral auxiliaries were designed and prepared.

  DOI：

  10.1021/jo801503c
• 作为产物：
  描述：

  propargyl 2-deoxy-3,4,6-tri-O-t-butyldimethylsilyl-β-D-galactopyranoside 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以69%的产率得到allenyl 2-deoxy-3,4,6-tri-O-t-butyldimethylsilyl-β-D-galactopyranoside
  参考文献：
  名称：

  Traceless Chiral Auxiliaries for the Allene Ether Nazarov Cyclization

  摘要：

  The key stereochemical factors that determine transfer of asymmetry from the chiral auxiliary to the cyclopentenone in the allene ether version of the Nazarov reaction have been elucidated. On the basis of the new insights into the mechanism, two highly effective chiral auxiliaries were designed and prepared.

  DOI：

  10.1021/jo801503c

文献信息

• Traceless Chiral Auxiliaries for the Allene Ether Nazarov Cyclization
  作者：April R. Banaag、Marcus A. Tius

  DOI：10.1021/jo801503c

  日期：2008.11.7

  The key stereochemical factors that determine transfer of asymmetry from the chiral auxiliary to the cyclopentenone in the allene ether version of the Nazarov reaction have been elucidated. On the basis of the new insights into the mechanism, two highly effective chiral auxiliaries were designed and prepared.