(2S,3R,4S,5R)-2-Hydroxymethyl-4-(4-methoxy-benzyloxy)-5-(4-methoxy-phenoxymethyl)-pyrrolidin-3-ol | 757244-59-0

• 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: (2S,3R,4S,5R)-2-Hydroxymethyl-4-(4-methoxy-benzyloxy)-5-(4-methoxy-phenoxymethyl)-pyrrolidin-3-ol
• CAS: 757244-59-0
• 化学式: C₂₁H₂₇NO₆
• 分子量: 389.448
• InChiKey: WMQKRLPQBDIGKZ-BQJUDKOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  89.41
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R)-2-Hydroxymethyl-4-(4-methoxy-benzyloxy)-5-(4-methoxy-phenoxymethyl)-pyrrolidin-3-ol 在 ammonium cerium(IV) nitrate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.17h， 生成 Acetic acid (2S,3R,4S,5R)-2-acetoxymethyl-1-acetyl-5-hydroxymethyl-4-(4-methoxy-benzyloxy)-pyrrolidin-3-yl ester
  参考文献：
  名称：

  Stereodivergent total asymmetric synthesis of polyhydroxylated pyrrolidines via tandem allylic epoxidation and intramolecular cyclization reactions

  摘要：

  Epoxidation of the allylic alcohols 10 and 11 using the VO(acac)(2)/t-BuOOH system followed by an intramolecular 5-exo cyclization of the resulting 8-epoxycarbamates 12, 13, 18, and 19 has been shown to provide a general and efficient solution for the asymmetric synthesis of polyhydroxy pyrrolidines. The requisite vicinal amino alcohol functionality was enantio-/regio-selectively installed by the Os-catalyzed asymmetric aminohydroxylation reaction of the designed achiral olefin 6. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.048
• 作为产物：
  描述：

  [(1R,2S,3S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-3-(R)-oxiranyl-propyl]-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 32.0h， 生成 (2S,3R,4S,5R)-2-Hydroxymethyl-4-(4-methoxy-benzyloxy)-5-(4-methoxy-phenoxymethyl)-pyrrolidin-3-ol
  参考文献：
  名称：

  Stereodivergent total asymmetric synthesis of polyhydroxylated pyrrolidines via tandem allylic epoxidation and intramolecular cyclization reactions

  摘要：

  Epoxidation of the allylic alcohols 10 and 11 using the VO(acac)(2)/t-BuOOH system followed by an intramolecular 5-exo cyclization of the resulting 8-epoxycarbamates 12, 13, 18, and 19 has been shown to provide a general and efficient solution for the asymmetric synthesis of polyhydroxy pyrrolidines. The requisite vicinal amino alcohol functionality was enantio-/regio-selectively installed by the Os-catalyzed asymmetric aminohydroxylation reaction of the designed achiral olefin 6. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.048