(2S)-2-benzyloxymethyl-4-(2-methylphenyl)-1-(4-methylphenylsulfonyl)-2,5-dihydro-1H-pyrrole | 920035-10-5

• 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: (2S)-2-benzyloxymethyl-4-(2-methylphenyl)-1-(4-methylphenylsulfonyl)-2,5-dihydro-1H-pyrrole
• 英文别名: (2S)-4-(2-methylphenyl)-1-(4-methylphenyl)sulfonyl-2-(phenylmethoxymethyl)-2,5-dihydropyrrole
• CAS: 920035-10-5
• 化学式: C₂₆H₂₇NO₃S
• 分子量: 433.571
• InChiKey: YFXRNNKZRDXKCK-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-2-benzyloxymethyl-4-(2-methylphenyl)-1-(4-methylphenylsulfonyl)-2,5-dihydro-1H-pyrrole 在 二异丁基氢化铝 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 (2R,3S,4S)-4-(2-methylphenyl)-1-(4-methylphenyl)sulfonyl-2-(phenylmethoxymethyl)pyrrolidin-3-ol
  参考文献：
  名称：

  Synthesis of (2R,3S,4S)-4-aryl-3-hydroxyprolinols

  摘要：

  Synthesis of (2R,3S,4S)-4-aryl-3-hydroxyprolinols has been established starting from 2-benzyloxymethylpyrrolidin-2-one framework, which is derived from commercially available trans-(2S,4R)-4-hydroxyproline. The single diastereorner having a trans-cis relative configuration with C-2 and C-3 and C-3 and C-4 is constructed in two one-pot functional group transformations of Grignard addition/dehydration and epoxidation/isomerization as the key steps in moderate yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.002
• 作为产物：
  描述：

  (2S,4R)-1-(4-methylphenyl)sulfonyl-2-hydroxymethyl-4-(t-butyldimethylsilanyloxy)pyrrolidine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 22.58h， 生成 (2S)-2-benzyloxymethyl-4-(2-methylphenyl)-1-(4-methylphenylsulfonyl)-2,5-dihydro-1H-pyrrole
  参考文献：
  名称：

  Synthesis of (2R,3S,4S)-4-aryl-3-hydroxyprolinols

  摘要：

  Synthesis of (2R,3S,4S)-4-aryl-3-hydroxyprolinols has been established starting from 2-benzyloxymethylpyrrolidin-2-one framework, which is derived from commercially available trans-(2S,4R)-4-hydroxyproline. The single diastereorner having a trans-cis relative configuration with C-2 and C-3 and C-3 and C-4 is constructed in two one-pot functional group transformations of Grignard addition/dehydration and epoxidation/isomerization as the key steps in moderate yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.002

文献信息

• Synthesis of (2R,3S,4S)-4-aryl-3-hydroxyprolinols
  作者：Meng-Yang Chang、Chun-Yu Lin、Tsun-Cheng Wu

  DOI：10.1016/j.tet.2006.10.002

  日期：2006.12

  Synthesis of (2R,3S,4S)-4-aryl-3-hydroxyprolinols has been established starting from 2-benzyloxymethylpyrrolidin-2-one framework, which is derived from commercially available trans-(2S,4R)-4-hydroxyproline. The single diastereorner having a trans-cis relative configuration with C-2 and C-3 and C-3 and C-4 is constructed in two one-pot functional group transformations of Grignard addition/dehydration and epoxidation/isomerization as the key steps in moderate yield. (c) 2006 Elsevier Ltd. All rights reserved.