(2S,3R,4S,5R)-2-hydroxymethyl-3,4-O-isopropylidene-5-(tert-butoxycarbonylmethyl)pyrrolidine | 1169755-38-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R)-2-hydroxymethyl-3,4-O-isopropylidene-5-(tert-butoxycarbonylmethyl)pyrrolidine
• CAS: 1169755-38-7
• 化学式: C₁₄H₂₅NO₅
• 分子量: 287.356
• InChiKey: UOSNWEMQRLRQJU-LLHIFLOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.57
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  77.02
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R)-2-hydroxymethyl-3,4-O-isopropylidene-5-(tert-butoxycarbonylmethyl)pyrrolidine 在 三氟乙酸 、 水 、 ammonium hydroxide 、 DOWEX 50WX₈-200 作用下， 以 水 为溶剂， 反应 4.0h， 以47%的产率得到(2'S,3'R,4'S,5'R)-(2'-hydroxymethyl-3',4'-dihydroxypyrrolidin-5'-yl)ethanoic acid
  参考文献：
  名称：

  Iodine-mediated ring-closing iodoamination with concomitant N-debenzylation for the asymmetric synthesis of polyhydroxylated pyrrolidines

  摘要：

  Treatment of a range of homochiral unsaturated beta-amino esters (containing a cis-dioxolane unit) with iodine promotes a novel ring-closing alkene iodoamination reaction which proceeds with concomitant N-debenzylation, providing a simple and stereoselective route to iodomethyl pyrrolidines. Functional group interconversion of the resulting iodomethyl pyrrolidines upon treatment with AgOAc proceeds via the corresponding aziridinium ion, with Subsequent deprotection giving access to polyhydroxylated pyrrolidines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.014
• 作为产物：
  描述：

  (2S,3R,4S,5R)-2-acetoxymethyl-3,4-O-isopropylidene-5-(tert-butoxycarbonylmethyl)pyrrolidine 在 potassium carbonate 、 水 、 氯化铵 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以94%的产率得到(2S,3R,4S,5R)-2-hydroxymethyl-3,4-O-isopropylidene-5-(tert-butoxycarbonylmethyl)pyrrolidine
  参考文献：
  名称：

  Iodine-mediated ring-closing iodoamination with concomitant N-debenzylation for the asymmetric synthesis of polyhydroxylated pyrrolidines

  摘要：

  Treatment of a range of homochiral unsaturated beta-amino esters (containing a cis-dioxolane unit) with iodine promotes a novel ring-closing alkene iodoamination reaction which proceeds with concomitant N-debenzylation, providing a simple and stereoselective route to iodomethyl pyrrolidines. Functional group interconversion of the resulting iodomethyl pyrrolidines upon treatment with AgOAc proceeds via the corresponding aziridinium ion, with Subsequent deprotection giving access to polyhydroxylated pyrrolidines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.014