(2R,3R)-4-benzyloxy-2,3-dimethylbutanal | 1041325-13-6

• 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: (2R,3R)-4-benzyloxy-2,3-dimethylbutanal
• 英文别名: (2R,3R)-2,3-dimethyl-4-phenylmethoxybutanal
• CAS: 1041325-13-6
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: NMKFPDYRRMHBAH-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  磷酰基乙酸三乙酯 、 (2R,3R)-4-benzyloxy-2,3-dimethylbutanal 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以89%的产率得到ethyl (2E,4S,5R)-6-benzyloxy-4,5-dimethyl-2-hexenoate
  参考文献：
  名称：

  Stereoselective synthesis of a C1–C6 fragment of pinnatoxin A via a 1,4-addition/alkylation sequence

  摘要：

  A C1-C6 fragment of pinnatoxin A, (5S,6R)-5,6-dimethyl-3-methyleneoxepan-2-one, which features a gamma,delta-trans-dimethyl-substituted alpha-methylene lactone, has been synthesized in an enantiomerically pure form from ethyl (E)-4-benzyloxy-2-butenoate through an auxiliary-based conjugate addition and alkylation reaction. The excellent diastereoselectivity (98:2) observed in the alkylation reaction is the result of stereocontrol from both the adjacent stereocenter and the chiral oxazolidinone. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.013
• 作为产物：
  描述：

  (2R,3R)-4-benzyloxy-2,3-dimethyl-1-butanol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以94%的产率得到(2R,3R)-4-benzyloxy-2,3-dimethylbutanal
  参考文献：
  名称：

  Stereoselective synthesis of a C1–C6 fragment of pinnatoxin A via a 1,4-addition/alkylation sequence

  摘要：

  A C1-C6 fragment of pinnatoxin A, (5S,6R)-5,6-dimethyl-3-methyleneoxepan-2-one, which features a gamma,delta-trans-dimethyl-substituted alpha-methylene lactone, has been synthesized in an enantiomerically pure form from ethyl (E)-4-benzyloxy-2-butenoate through an auxiliary-based conjugate addition and alkylation reaction. The excellent diastereoselectivity (98:2) observed in the alkylation reaction is the result of stereocontrol from both the adjacent stereocenter and the chiral oxazolidinone. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.013