propan-2-yl (3R)-3-hydroxy-4-phenylmethoxybutanoate | 216868-11-0

• 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: propan-2-yl (3R)-3-hydroxy-4-phenylmethoxybutanoate
• CAS: 216868-11-0
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: OEBMZJIXLCTVGO-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  propan-2-yl (3R)-3-hydroxy-4-phenylmethoxybutanoate 、 碘甲烷 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 propan-2-yl (2R,3R)-3-hydroxy-2-methyl-4-phenylmethoxybutanoate 、 propan-2-yl (2S,3R)-3-hydroxy-2-methyl-4-phenylmethoxybutanoate
  参考文献：
  名称：

  An efficient protocol for the stereoselective dihydroxylation of ene-ester systems

  摘要：

  Dihydroxylation of ene ester systems was achieved in good yield and diastereoselectivity under classical catalytic OsO4 and NMO conditions using the intrinsic diastereoselectivity in alpha-methyl beta-OTBS systems. This intrinsic diastereoselection can be reversed using 'super' AD-mix to give the opposite diastereomer also in good selectivity. The regioselection of dihydroxylation in diene esters using a modified 'super' AD-mix was poor. This methodology can be applied towards the synthesis of part structures of the marine macrolide Altohyrtin A. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00800-x
• 作为产物：
  描述：

  4-benzyloxyacetoacetic acid isopropyl ester 在 (R)-RuCl₂(2,2'-bis(di(tolylphosphanyl)-1,1'-binaphthyl) 、 氢气 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 24.0h， 以100%的产率得到propan-2-yl (3R)-3-hydroxy-4-phenylmethoxybutanoate
  参考文献：
  名称：

  An efficient protocol for the stereoselective dihydroxylation of ene-ester systems

  摘要：

  Dihydroxylation of ene ester systems was achieved in good yield and diastereoselectivity under classical catalytic OsO4 and NMO conditions using the intrinsic diastereoselectivity in alpha-methyl beta-OTBS systems. This intrinsic diastereoselection can be reversed using 'super' AD-mix to give the opposite diastereomer also in good selectivity. The regioselection of dihydroxylation in diene esters using a modified 'super' AD-mix was poor. This methodology can be applied towards the synthesis of part structures of the marine macrolide Altohyrtin A. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00800-x

文献信息

• An efficient protocol for the stereoselective dihydroxylation of ene-ester systems
  作者：Stephen A. Hermitage、Alison Murphy、Poul Nielsen、Stanley M. Roberts

  DOI：10.1016/s0040-4020(98)00800-x

  日期：1998.10

  Dihydroxylation of ene ester systems was achieved in good yield and diastereoselectivity under classical catalytic OsO4 and NMO conditions using the intrinsic diastereoselectivity in alpha-methyl beta-OTBS systems. This intrinsic diastereoselection can be reversed using 'super' AD-mix to give the opposite diastereomer also in good selectivity. The regioselection of dihydroxylation in diene esters using a modified 'super' AD-mix was poor. This methodology can be applied towards the synthesis of part structures of the marine macrolide Altohyrtin A. (C) 1998 Elsevier Science Ltd. All rights reserved.