[(3aR,5R,6S,6aR)-2,2-dimethyl-5-(phenylmethoxymethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] (4R)-4-bromooctanoate | 568579-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(3aR,5R,6S,6aR)-2,2-dimethyl-5-(phenylmethoxymethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] (4R)-4-bromooctanoate
• CAS: 568579-46-4
• 化学式: C₂₃H₃₃BrO₆
• 分子量: 485.415
• InChiKey: HMSKJZVSYACJMS-VBCWZRPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3aR,5R,6S,6aR)-2,2-dimethyl-5-(phenylmethoxymethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] (4R)-4-bromooctanoate 在 lithium hydroxide 、 双氧水 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (S)-4-butylbutanolide 、 (R)-5-正丁基二氢呋喃-2-酮
  参考文献：
  名称：

  An asymmetric Kharasch reaction mediated by d-xylose: long range diastereocontrol

  摘要：

  An asymmetric Kharasch-type atom transfer reaction was studied under 13 different sets of reaction conditions in order to obtain the highest levels of diastereoselection. The highest ratio of 12.5:1 (71%) was observed at low temperatures (-78degreesC) using the Lewis acid Eu(OTf)(3). Because the new asymmetric center is so distant from the D-xylose, we propose a transition state involving two sugars. The conversion of the major product to a naturally occurring chiral gamma-butyrolactone, under basic conditions, is described which also confirmed the diastereoselectivity and absolute stereochemistry of the Kharasch reaction. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00756-1
• 作为产物：
  描述：

  1,2:3,5-双-O-异亚丙基-alpha-D-呋喃木糖 在 4-二甲氨基吡啶 、 三乙基硼 、 europium(III) trifluoroacetate 、 氧气 、 sodium hydride 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 [(3aR,5R,6S,6aR)-2,2-dimethyl-5-(phenylmethoxymethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] (4R)-4-bromooctanoate
  参考文献：
  名称：

  An asymmetric Kharasch reaction mediated by d-xylose: long range diastereocontrol

  摘要：

  An asymmetric Kharasch-type atom transfer reaction was studied under 13 different sets of reaction conditions in order to obtain the highest levels of diastereoselection. The highest ratio of 12.5:1 (71%) was observed at low temperatures (-78degreesC) using the Lewis acid Eu(OTf)(3). Because the new asymmetric center is so distant from the D-xylose, we propose a transition state involving two sugars. The conversion of the major product to a naturally occurring chiral gamma-butyrolactone, under basic conditions, is described which also confirmed the diastereoselectivity and absolute stereochemistry of the Kharasch reaction. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00756-1

文献信息

• An asymmetric Kharasch reaction mediated by d-xylose: long range diastereocontrol
  作者：Eric J. Enholm、Ashwin Bhardawaj

  DOI：10.1016/s0040-4039(03)00756-1

  日期：2003.5

  An asymmetric Kharasch-type atom transfer reaction was studied under 13 different sets of reaction conditions in order to obtain the highest levels of diastereoselection. The highest ratio of 12.5:1 (71%) was observed at low temperatures (-78degreesC) using the Lewis acid Eu(OTf)(3). Because the new asymmetric center is so distant from the D-xylose, we propose a transition state involving two sugars. The conversion of the major product to a naturally occurring chiral gamma-butyrolactone, under basic conditions, is described which also confirmed the diastereoselectivity and absolute stereochemistry of the Kharasch reaction. (C) 2003 Elsevier Science Ltd. All rights reserved.