({(1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(phenylseleno)methyl]ethyl}oxy)acetaldehyde | 936251-83-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: ({(1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(phenylseleno)methyl]ethyl}oxy)acetaldehyde
• 英文别名: 2-[(2R)-1-[tert-butyl(diphenyl)silyl]oxy-3-phenylselanylpropan-2-yl]oxyacetaldehyde
• CAS: 936251-83-1
• 化学式: C₂₇H₃₂O₃SeSi
• 分子量: 511.595
• InChiKey: KYKSFGPZNOITGH-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ({(1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(phenylseleno)methyl]ethyl}oxy)acetaldehyde 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以40%的产率得到(3S,5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Intramolecular addition of carbon radicals to aldehydes: synthesis of enantiopure tetrahydrofuran-3-ols

  摘要：

  A simple and efficient substrate-controlled asymmetric synthesis of enantiopure tetrahydrofuran-3-ols by a 5-exo-trig radical cyclization is described. This cyclization occurs when a delta-carbon radical adds intramolecularly to the carbonyl group of an aldehyde. The delta-carbon radicals can be efficiently produced from the tin hydride mediated deselenenylation of 5-phenylseleno-3-oxapentanals, which were easily prepared starting from commercially available enantiopure epoxides or chlorohydrins. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.047
• 作为产物：
  描述：

  (2R)-1-{[tert-butyl(diphenyl)silyl]oxy}-3-(phenylseleno)propan-2-ol 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 甲苯 、 苯 为溶剂， 反应 1.0h， 生成 ({(1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(phenylseleno)methyl]ethyl}oxy)acetaldehyde
  参考文献：
  名称：

  Intramolecular addition of carbon radicals to aldehydes: synthesis of enantiopure tetrahydrofuran-3-ols

  摘要：

  A simple and efficient substrate-controlled asymmetric synthesis of enantiopure tetrahydrofuran-3-ols by a 5-exo-trig radical cyclization is described. This cyclization occurs when a delta-carbon radical adds intramolecularly to the carbonyl group of an aldehyde. The delta-carbon radicals can be efficiently produced from the tin hydride mediated deselenenylation of 5-phenylseleno-3-oxapentanals, which were easily prepared starting from commercially available enantiopure epoxides or chlorohydrins. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.047

文献信息

• Intramolecular addition of carbon radicals to aldehydes: synthesis of enantiopure tetrahydrofuran-3-ols
  作者：Marcello Tiecco、Lorenzo Testaferri、Francesca Marini、Silvia Sternativo、Claudio Santi、Luana Bagnoli、Andrea Temperini

  DOI：10.1016/j.tet.2007.04.047

  日期：2007.6

  A simple and efficient substrate-controlled asymmetric synthesis of enantiopure tetrahydrofuran-3-ols by a 5-exo-trig radical cyclization is described. This cyclization occurs when a delta-carbon radical adds intramolecularly to the carbonyl group of an aldehyde. The delta-carbon radicals can be efficiently produced from the tin hydride mediated deselenenylation of 5-phenylseleno-3-oxapentanals, which were easily prepared starting from commercially available enantiopure epoxides or chlorohydrins. (c) 2007 Elsevier Ltd. All rights reserved.