(2R,3S,4S,5R)-3-Hydroxy-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-5-(4-methoxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | 757244-56-7

• 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,3S,4S,5R)-3-Hydroxy-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-5-(4-methoxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS: 757244-56-7
• 化学式: C₂₆H₃₅NO₈
• 分子量: 489.566
• InChiKey: PJIRWTQHWHRVJP-LWSSLDFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106.92
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R)-3-Hydroxy-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-5-(4-methoxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 在 盐酸 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.17h， 生成 (2R,3S,4S,5R)-2,5-Bis-hydroxymethyl-pyrrolidine-3,4-diol; hydrochloride
  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：

  ethyl (2S,3R)-3-acetamido-2-hydroxy-4-(4-methoxyphenoxy)butanoate 在 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 bis(acetylacetonate)oxovanadium 、 sodium hydride 、 二异丁基氢化铝 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 癸烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 39.0h， 生成 (2R,3S,4S,5R)-3-Hydroxy-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-5-(4-methoxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl 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