Acetic acid (2S,3R,4S,5R)-2-acetoxymethyl-1-acetyl-4-(4-methoxy-benzyloxy)-5-(4-methoxy-phenoxymethyl)-pyrrolidin-3-yl ester | 757244-60-3

• 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: Acetic acid (2S,3R,4S,5R)-2-acetoxymethyl-1-acetyl-4-(4-methoxy-benzyloxy)-5-(4-methoxy-phenoxymethyl)-pyrrolidin-3-yl ester
• CAS: 757244-60-3
• 化学式: C₂₇H₃₃NO₉
• 分子量: 515.56
• InChiKey: ATXPPQIDIFMQLS-LGTXBLIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  109.83
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4S,5R)-2-acetoxymethyl-1-acetyl-4-(4-methoxy-benzyloxy)-5-(4-methoxy-phenoxymethyl)-pyrrolidin-3-yl ester 在 盐酸 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.17h， 生成 2,5-dideoxy-2,5-imino-D-galactitol 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：

  乙酸酐 、 (2S,3R,4S,5R)-2-Hydroxymethyl-4-(4-methoxy-benzyloxy)-5-(4-methoxy-phenoxymethyl)-pyrrolidin-3-ol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到Acetic acid (2S,3R,4S,5R)-2-acetoxymethyl-1-acetyl-4-(4-methoxy-benzyloxy)-5-(4-methoxy-phenoxymethyl)-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