methyl (2R,3S)-2-[tert-butyl(dimethyl)silyl]oxy-3-chlorobutanoate | 1040921-80-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2R,3S)-2-[tert-butyl(dimethyl)silyl]oxy-3-chlorobutanoate
• CAS: 1040921-80-9
• 化学式: C₁₁H₂₃ClO₃Si
• 分子量: 266.84
• InChiKey: DOFBLPGASPQPQU-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  methyl (2R,3S)-2-[tert-butyl(dimethyl)silyl]oxy-3-chlorobutanoate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以88%的产率得到(2R,3S)-2-[tert-butyl(dimethyl)silyl]oxy-3-chlorobutan-1-ol
  参考文献：
  名称：

  Total synthesis of (+)-asperlin

  摘要：

  Syntheses of (+)-asperlin 1 were achieved via two different synthetic routes. 1,2-Addition of alpha-furyl anion to (2R,3S)-2-'butyldimethylsilyloxy-3-chlorobutanal 6 gave (1S,2R,3S)-1-(2-furyl)-2-'butyldimethylsilyloxy-3-chlorobutanol 7, which was converted to the chiral intermediate, (1S,2R,3R)-1-(2-furyl)-2,3-epoxybutanol 8 (37% overall yield from 6) for the synthesis of (+)-1. The second synthesis of (+)-asperlin 1 from (2R,3S)-6 was achieved in 8% overall yield, based on a combination of the indium-assisted stereoselective addition of 3-bromopropenyl acetate 9 to (2R,3S)-6 and the ring closing metathesis (RCM) using Grubbs catalyst. (C) 2008 Elsevier Ltd. All riehts reserved.

  DOI：

  10.1016/j.tetasy.2008.04.011
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 methyl (2R,3S)-3-chloro-2-hydroxybutanoate 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以92%的产率得到methyl (2R,3S)-2-[tert-butyl(dimethyl)silyl]oxy-3-chlorobutanoate
  参考文献：
  名称：

  Total synthesis of (+)-asperlin

  摘要：

  Syntheses of (+)-asperlin 1 were achieved via two different synthetic routes. 1,2-Addition of alpha-furyl anion to (2R,3S)-2-'butyldimethylsilyloxy-3-chlorobutanal 6 gave (1S,2R,3S)-1-(2-furyl)-2-'butyldimethylsilyloxy-3-chlorobutanol 7, which was converted to the chiral intermediate, (1S,2R,3R)-1-(2-furyl)-2,3-epoxybutanol 8 (37% overall yield from 6) for the synthesis of (+)-1. The second synthesis of (+)-asperlin 1 from (2R,3S)-6 was achieved in 8% overall yield, based on a combination of the indium-assisted stereoselective addition of 3-bromopropenyl acetate 9 to (2R,3S)-6 and the ring closing metathesis (RCM) using Grubbs catalyst. (C) 2008 Elsevier Ltd. All riehts reserved.

  DOI：

  10.1016/j.tetasy.2008.04.011

文献信息

• Total synthesis of (+)-asperlin
  作者：Hideaki Akaike、Hidekazu Horie、Keisuke Kato、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2008.04.011

  日期：2008.5

  Syntheses of (+)-asperlin 1 were achieved via two different synthetic routes. 1,2-Addition of alpha-furyl anion to (2R,3S)-2-'butyldimethylsilyloxy-3-chlorobutanal 6 gave (1S,2R,3S)-1-(2-furyl)-2-'butyldimethylsilyloxy-3-chlorobutanol 7, which was converted to the chiral intermediate, (1S,2R,3R)-1-(2-furyl)-2,3-epoxybutanol 8 (37% overall yield from 6) for the synthesis of (+)-1. The second synthesis of (+)-asperlin 1 from (2R,3S)-6 was achieved in 8% overall yield, based on a combination of the indium-assisted stereoselective addition of 3-bromopropenyl acetate 9 to (2R,3S)-6 and the ring closing metathesis (RCM) using Grubbs catalyst. (C) 2008 Elsevier Ltd. All riehts reserved.