(S)-3-O-(2-methoxyethoxymethyl)-3-hydroxybutanal | 225781-24-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-O-(2-methoxyethoxymethyl)-3-hydroxybutanal
• 英文别名: (3S)-3-(2-methoxyethoxymethoxy)butanal
• CAS: 225781-24-8
• 化学式: C₈H₁₆O₄
• 分子量: 176.213
• InChiKey: KVYNPHWHICBNRN-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-O-(2-methoxyethoxymethyl)-3-hydroxybutanal 在 2,4,6-三硝基氯苯 作用下， 以 吡啶 为溶剂， 生成 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,3S)-1-ethyl-3-(2-methoxy-ethoxymethoxy)-butyl ester
  参考文献：
  名称：

  Application of the modified Mosher's method to linear 1,3-diols

  摘要：

  Absolute configurations of linear 1,3-diols can be determined by NMR spectroscopy by means of the modified Mosher's method. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00404-9
• 作为产物：
  描述：

  (S)-1-O-acetyl-3-O-(2-methoxyethoxymethyl)-1,3-butanediol 在 4 A molecular sieve 、 sodium methylate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.33h， 生成 (S)-3-O-(2-methoxyethoxymethyl)-3-hydroxybutanal
  参考文献：
  名称：

  Lipase mediated resolution of 1,3-butanediol derivatives: chiral building blocks for pheromone enantiosynthesis. Part 3

  摘要：

  (R,S)-1,3-butanediol 5 was kinetically resolved by enzymatic acetylation with vinyl acetate under the presence of Chirazyme (TM) L-2, c-f, yielding (S)-1-O-acetyl-1,3-hydroxybutane 6 and (R)-1,3-di-O-acetyl-1,3-butanediol 7 with enantiomeric excesses of 91%, (E=67.3). Compounds 6 and 7 were easily transformed into the corresponding (S)-3-O-(2-methoxyethoxymethyl)-3-hydroxybutanal 10 and (R)-3-benzyloxybutanal 19, through a protection-deprotection and functional group interchange methodology. Subsequent reaction of 10 and 19 with 3-(methoxycarbonlypropionyl-methylene)triphenylphosphorane afforded methyl (E,S)-8-O-(2-methoxyethoxymethyl)-4-oxo-5-nonenoate 12 and (E,R)-8-benzyl-oxy-4-oxo-5-nonenoate 20. The alkenes 19 and 20 were then catalytically hydrogenated to the corresponding saturated eaters 13 and 21. Treatment of 13 and 21 with 1,2-ethanedithiol/F3B . OEt2 afforded dithioketals 14 and 22, which were respectively reduced to (S)-1,8-dihydroxy-4-nonanone ethylidenedithioketal 15 and (R)-8-O-benzyl-1,8-dihydroxy-4-nonanone ethylidenedithioketal 23. Finally, deprotection of 15 by catalytic hydrogenation under acidic conditions gave the expected (5S,7S)-(-)-7-methy1-1,6-dioxaspiro[4.5]decane 1. The (5R,7R)-(+)-1 enantiomer was analogously prepared fi om 23. Both compounds were formed by this procedure with an e.e. of 91%. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00038-6

文献信息

• Application of the modified Mosher's method to linear 1,3-diols
  作者：Kyoji Kouda、Takashi Ooi、Takenori Kusumi

  DOI：10.1016/s0040-4039(99)00404-9

  日期：1999.4

  Absolute configurations of linear 1,3-diols can be determined by NMR spectroscopy by means of the modified Mosher's method. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Lipase mediated resolution of 1,3-butanediol derivatives: chiral building blocks for pheromone enantiosynthesis. Part 3
  作者：Isidoro Izquierdo、Marı́a T. Plaza、Miguel Rodrı́guez、Juan A. Tamayo、Alicia Martos

  DOI：10.1016/s0957-4166(01)00038-6

  日期：2001.2

  (R,S)-1,3-butanediol 5 was kinetically resolved by enzymatic acetylation with vinyl acetate under the presence of Chirazyme (TM) L-2, c-f, yielding (S)-1-O-acetyl-1,3-hydroxybutane 6 and (R)-1,3-di-O-acetyl-1,3-butanediol 7 with enantiomeric excesses of 91%, (E=67.3). Compounds 6 and 7 were easily transformed into the corresponding (S)-3-O-(2-methoxyethoxymethyl)-3-hydroxybutanal 10 and (R)-3-benzyloxybutanal 19, through a protection-deprotection and functional group interchange methodology. Subsequent reaction of 10 and 19 with 3-(methoxycarbonlypropionyl-methylene)triphenylphosphorane afforded methyl (E,S)-8-O-(2-methoxyethoxymethyl)-4-oxo-5-nonenoate 12 and (E,R)-8-benzyl-oxy-4-oxo-5-nonenoate 20. The alkenes 19 and 20 were then catalytically hydrogenated to the corresponding saturated eaters 13 and 21. Treatment of 13 and 21 with 1,2-ethanedithiol/F3B . OEt2 afforded dithioketals 14 and 22, which were respectively reduced to (S)-1,8-dihydroxy-4-nonanone ethylidenedithioketal 15 and (R)-8-O-benzyl-1,8-dihydroxy-4-nonanone ethylidenedithioketal 23. Finally, deprotection of 15 by catalytic hydrogenation under acidic conditions gave the expected (5S,7S)-(-)-7-methy1-1,6-dioxaspiro[4.5]decane 1. The (5R,7R)-(+)-1 enantiomer was analogously prepared fi om 23. Both compounds were formed by this procedure with an e.e. of 91%. (C) 2001 Elsevier Science Ltd. All rights reserved.