allenyl 4,6-O-benzylidene-3-O-t-butyldimethylsilyl-2-deoxy-α-D-allopyranoside | 940933-72-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: allenyl 4,6-O-benzylidene-3-O-t-butyldimethylsilyl-2-deoxy-α-D-allopyranoside
• 英文别名: t-butyldimethyl((2R,4aR,6S,8S,8aR)-2-phenyl-6-(propa-1,2-dienyloxy)hexahydropyrano[3,2-d][1,3]dioxin-8-yloxy)silane
• CAS: 940933-72-2
• 化学式: C₂₂H₃₂O₅Si
• 分子量: 404.579
• InChiKey: LXWBYBIDSIAOJV-HGJUEJDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 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 4,6-O-benzylidene-3-O-t-butyldimethylsilyl-2-deoxy-α-D-allopyranoside 、 (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90%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 2,3:4,6-di-O-benzylidene-D-mannopyranoside 在 吡啶 、 正丁基锂 、 potassium tert-butylate 、 叔丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 正戊烷 为溶剂， 反应 4.08h， 生成 allenyl 4,6-O-benzylidene-3-O-t-butyldimethylsilyl-2-deoxy-α-D-allopyranoside
  参考文献：
  名称：

  Design of Chiral Auxiliaries for the Allene Ether Nazarov Cyclization

  摘要：

  A 1,3- or a 1,4-cis axial tert-butyldimethylsilyloxy substituent on the pyranose derived chiral auxiliary for the allene ether Nazarov cyclization leads to products in high optical purity. alpha-Pyranose and beta-pyranose derived auxiliaries lead to enantiomeric products.

  DOI：

  10.1021/ja069342g

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

  DOI：10.1021/ja069342g

  日期：2007.5.1

  A 1,3- or a 1,4-cis axial tert-butyldimethylsilyloxy substituent on the pyranose derived chiral auxiliary for the allene ether Nazarov cyclization leads to products in high optical purity. alpha-Pyranose and beta-pyranose derived auxiliaries lead to enantiomeric products.