5-<(2S)-2-(tert-butyldimethylsilyl)oxy-1-iodopropyl>-2-methyl-3-ethoxycarbonyl-4,5-dihydrofuran | 243841-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 5-<(2S)-2-(tert-butyldimethylsilyl)oxy-1-iodopropyl>-2-methyl-3-ethoxycarbonyl-4,5-dihydrofuran
• CAS: 243841-22-7
• 化学式: C₁₇H₃₁IO₄Si
• 分子量: 454.421
• InChiKey: UKNJDKUGYRKNAI-GRTSSRMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-<(2S)-2-(tert-butyldimethylsilyl)oxy-1-iodopropyl>-2-methyl-3-ethoxycarbonyl-4,5-dihydrofuran 在 偶氮二异丁腈 、 氧气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 96.0h， 生成 5-<(2S,1R)-2-(tert-butyldimethylsilyl)oxy-1-hydroxypropyl>-2-methyl-3-ethoxycarbonyl furan
  参考文献：
  名称：

  Diastereoselective synthesis of enantiopure 5-[2-(alkoxyalkyl)-1-(hydroperoxypropyl)]-3-alkoxycarbonyl-2-alkyl furans

  摘要：

  The diastereoselective approach to enantiomerically pure furyl hydroperoxides of general type 1 has been accomplished starting from (S)-(-)-ethyl lactate. In the first part of the synthesis the alkylating reagents 7a,b were efficiently produced to be used in the second part for a 4-step known methodology to obtain furyl hydroperoxides. The most relevant transformation of the synthesis is the first reported diastereoselective iodoenoletherification of 2-acetyl-4-heptenoate esters 8a,b possessing a phi-chiral center. Furthermore, the final radical oxidation performed on (E)-5-alkylidene-4,5-dihydrofurans 11a,b led to formation of hydroperoxides (S,S)-12a,b in a diastereocontrolled manner due to 1,2-asymmetric induction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00187-1
• 作为产物：
  描述：

  ethyl 2-acetyl-(4E,6S)-6-<(tert-butyldimethylsilyl)oxy>-4-heptenoate 在 碘 、 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (+/-)-2-methyl-5-(E)-propenyl-3-ethoxycarbonyl-4,5-dihydrofuran 、 5-<(2S)-2-(tert-butyldimethylsilyl)oxy-1-iodopropyl>-2-methyl-3-ethoxycarbonyl-4,5-dihydrofuran
  参考文献：
  名称：

  Diastereoselective synthesis of enantiopure 5-[2-(alkoxyalkyl)-1-(hydroperoxypropyl)]-3-alkoxycarbonyl-2-alkyl furans

  摘要：

  The diastereoselective approach to enantiomerically pure furyl hydroperoxides of general type 1 has been accomplished starting from (S)-(-)-ethyl lactate. In the first part of the synthesis the alkylating reagents 7a,b were efficiently produced to be used in the second part for a 4-step known methodology to obtain furyl hydroperoxides. The most relevant transformation of the synthesis is the first reported diastereoselective iodoenoletherification of 2-acetyl-4-heptenoate esters 8a,b possessing a phi-chiral center. Furthermore, the final radical oxidation performed on (E)-5-alkylidene-4,5-dihydrofurans 11a,b led to formation of hydroperoxides (S,S)-12a,b in a diastereocontrolled manner due to 1,2-asymmetric induction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00187-1

文献信息

• Diastereoselective synthesis of enantiopure 5-[2-(alkoxyalkyl)-1-(hydroperoxypropyl)]-3-alkoxycarbonyl-2-alkyl furans
  作者：Alessandra Lattanzi、Francesco Sagulo、Arrigo Scettri

  DOI：10.1016/s0957-4166(99)00187-1

  日期：1999.5

  The diastereoselective approach to enantiomerically pure furyl hydroperoxides of general type 1 has been accomplished starting from (S)-(-)-ethyl lactate. In the first part of the synthesis the alkylating reagents 7a,b were efficiently produced to be used in the second part for a 4-step known methodology to obtain furyl hydroperoxides. The most relevant transformation of the synthesis is the first reported diastereoselective iodoenoletherification of 2-acetyl-4-heptenoate esters 8a,b possessing a phi-chiral center. Furthermore, the final radical oxidation performed on (E)-5-alkylidene-4,5-dihydrofurans 11a,b led to formation of hydroperoxides (S,S)-12a,b in a diastereocontrolled manner due to 1,2-asymmetric induction. (C) 1999 Elsevier Science Ltd. All rights reserved.