1-O-allenyl-3,4,6-tri-O-t-butyldimethylsilyl-2-deoxy-α-D-glucopyranoside | 899446-48-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-allenyl-3,4,6-tri-O-t-butyldimethylsilyl-2-deoxy-α-D-glucopyranoside
• 英文别名: allenyl 2-deoxy-3,4,6-tri-O-t-butyldimethylsilyl-α-D-glucopyranoside
• CAS: 899446-48-1
• 化学式: C₂₇H₅₆O₅Si₃
• 分子量: 544.995
• InChiKey: BOKFEBHFHABIPC-LWSSLDFYSA-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：

  2-methyl-1-morpholin-4-ylpent-2-en-1-one 、 1-O-allenyl-3,4,6-tri-O-t-butyldimethylsilyl-2-deoxy-α-D-glucopyranoside 在 盐酸 正丁基锂 、 1,10-菲罗啉 、 lithium chloride 、 六氟异丙醇 、 乙酰氯 作用下， 以 四氢呋喃 、 正己烷 、 2,2,2-三氟乙醇 为溶剂， 反应 2.75h， 生成 (4S)-4-ethyl-2-hydroxy-3-methyl-5-methylidenecyclopent-2-en-1-one 、 (4R)-4-ethyl-2-hydroxy-3-methyl-5-methylidenecyclopent-2-en-1-one
  参考文献：
  名称：

  An Improved Chiral Auxiliary for the Allene Ether Version of the Nazarov Cyclization

  摘要：

  alpha-2-Deoxy-D-glucose derived ether 14 is a superior reagent for the allene ether version of the Nazarov cyclization. Enantiomeric excesses of products derived from trisubstituted morpholino enamides varied between 85% and 93% ee.

  DOI：

  10.1021/ol060816q
• 作为产物：
  描述：

  2-Deoxy-D-glucose 在 吡啶 、 三氟化硼乙醚 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1-O-allenyl-3,4,6-tri-O-t-butyldimethylsilyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  An Improved Chiral Auxiliary for the Allene Ether Version of the Nazarov Cyclization

  摘要：

  alpha-2-Deoxy-D-glucose derived ether 14 is a superior reagent for the allene ether version of the Nazarov cyclization. Enantiomeric excesses of products derived from trisubstituted morpholino enamides varied between 85% and 93% ee.

  DOI：

  10.1021/ol060816q

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.
• An Improved Chiral Auxiliary for the Allene Ether Version of the Nazarov Cyclization
  作者：Derrick B. delos Santos、April R. Banaag、Marcus A. Tius

  DOI：10.1021/ol060816q

  日期：2006.6.1

  alpha-2-Deoxy-D-glucose derived ether 14 is a superior reagent for the allene ether version of the Nazarov cyclization. Enantiomeric excesses of products derived from trisubstituted morpholino enamides varied between 85% and 93% ee.