[(2R,3R,4R)-3-氨基-2,4-吡咯烷二基]二甲醇 | 155935-60-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: [(2R,3R,4R)-3-氨基-2,4-吡咯烷二基]二甲醇
• 英文名称: ((2R,3R,4R)-3-Amino-4-hydroxymethyl-pyrrolidin-2-yl)-methanol
• 英文别名: [(3R,4R,5R)-4-Amino-5-(hydroxymethyl)pyrrolidin-3-YL]methanol
• CAS: 155935-60-7
• 化学式: C₆H₁₄N₂O₂
• 分子量: 146.189
• InChiKey: GKRGFUWLYFZLKY-HCWXCVPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  78.5
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  硫代异氰酸苯酯 、 [(2R,3R,4R)-3-氨基-2,4-吡咯烷二基]二甲醇 以 乙酸乙酯 为溶剂， 反应 72.0h， 以27%的产率得到(2R,3R,4R)-2,4-Bis-hydroxymethyl-3-(3-phenyl-thioureido)-pyrrolidine-1-carbothioic acid phenylamide
  参考文献：
  名称：

  IOOC Route to Substituted Chiral Pyrrolidines. Potential Glycosidase Inhibitors

  摘要：

  Branched-chain five-membered ring aza-sugar analogues, synthesized from amino acids by an intramolecular oxime-olefin cycloaddition reaction, the IOOC route, were found to be selective glycosidase inhibitors. The derivative 2,4(S)-di(hydroxymethyl)-3(S)-aminopyrrolidine, obtained from D-serine, was about 1 order of potency more active than its enantiomer obtained from L-serine.

  DOI：

  10.1021/jo9815094
• 作为产物：
  描述：

  (3aR,3bR,7aR)-Hexahydro-2,5-dioxa-3,6a-diaza-cyclopenta[a]pentalen-6-one 在 Ra-Ni caesium carbonate 作用下， 以 甲醇 、 水 为溶剂， 生成 [(2R,3R,4R)-3-氨基-2,4-吡咯烷二基]二甲醇
  参考文献：
  名称：

  L-丝氨酸在肟烯烃环加成路线中用于官能化的不对称吡咯烷，一种选择性的α-葡萄糖苷酶抑制剂

  摘要：

  从L-丝氨酸开始并利用分子内肟肟烯烃环加成反应的不对称氮杂糖类似物的新途径已成功开发。该支链糖氨基二（羟甲基）吡咯烷家族的成员（1和2）表现出对α-葡糖苷酶的选择性抑制，而未检测到对β-葡糖苷酶的抑制。

  DOI：

  10.1016/0040-4039(94)85229-4

文献信息

• Utilization of L-serine in an oxime olefin cycloaddition route to a functionalized asymmetric pyrrolidine, a selective α-glucosidase inhibitor
  作者：Alfred Hassner、Eliezer Falb、Abraham Nudelman、Amnon Albeck、Hugo E. Gottlieb

  DOI：10.1016/0040-4039(94)85229-4

  日期：1994.4

  A new route for asymmetric aza-sugar analogs starting with L-serine and utilizing an intramolecular oxime olefin cycloaddition has been successfully developed. A member of this family of branched chain sugar amino di(hydroxymethyl) pyrrolidines (1 and 2) exhibits selective inhibition of α-glucosidase, while no inhibition of β-glucosidase was detected.

  从L-丝氨酸开始并利用分子内肟肟烯烃环加成反应的不对称氮杂糖类似物的新途径已成功开发。该支链糖氨基二（羟甲基）吡咯烷家族的成员（1和2）表现出对α-葡糖苷酶的选择性抑制，而未检测到对β-葡糖苷酶的抑制。
• IOOC Route to Substituted Chiral Pyrrolidines. Potential Glycosidase Inhibitors
  作者：Eliezer Falb、Yosi Bechor、Abraham Nudelman、Alfred Hassner、Amnon Albeck、Hugo E. Gottlieb

  DOI：10.1021/jo9815094

  日期：1999.1.1

  Branched-chain five-membered ring aza-sugar analogues, synthesized from amino acids by an intramolecular oxime-olefin cycloaddition reaction, the IOOC route, were found to be selective glycosidase inhibitors. The derivative 2,4(S)-di(hydroxymethyl)-3(S)-aminopyrrolidine, obtained from D-serine, was about 1 order of potency more active than its enantiomer obtained from L-serine.