(3R,5S)-1-benzyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-3-yl methanesulfonate | 627100-77-0

• 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: (3R,5S)-1-benzyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-3-yl methanesulfonate
• 英文别名: [(3R,5S)-1-benzyl-5-[[tert-butyl(dimethyl)silyl]oxymethyl]pyrrolidin-3-yl] methanesulfonate
• CAS: 627100-77-0
• 化学式: C₁₉H₃₃NO₄SSi
• 分子量: 399.627
• InChiKey: DWUZFQNHHAHOKL-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,5S)-1-benzyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-3-yl methanesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以53%的产率得到(2S,4S)-4-azido-1-benzyl-2-(tert-butyldimethylsilyloxymethyl)pyrrolidine
  参考文献：
  名称：

  Ex-chiral pool synthesis and receptor binding studies of 4-substituted prolinol derivatives

  摘要：

  Starting from natural 4-hydroxyproline, preparation of the four possible stereoisomers of 4-amino- and 4-aminomethyl-substituted prolinol derivatives, respectively, was accomplished by chemo- and regioselective functional group transformations at the 2- and 4-positions of the pyrrolidine moiety. These building blocks were used as valuable precursors for the preparation of new methoxybenzamide derivatives. Dopamine and serotonin binding studies involving the subtypes D1, D2(long), D2(short), D3 and D4 as well as 5-HT1(A) and 5-HT2 respectively, displayed interesting structure activity relationships, especially with respect to the absolute and relative configuration of the test compounds. As a complement to the D3 receptor preferring aminomethylpyrrolidine FAUC 21. the (2R,4R)-aminoprolinol derivative ent-24 (FAUC 65) preferentially recognizing the D4 subtype was developed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.019
• 作为产物：
  描述：

  (4R)-4-羟基-L-脯氨酸盐酸盐 在 咪唑 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 (3R,5S)-1-benzyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-3-yl methanesulfonate
  参考文献：
  名称：

  Ex-chiral pool synthesis and receptor binding studies of 4-substituted prolinol derivatives

  摘要：

  Starting from natural 4-hydroxyproline, preparation of the four possible stereoisomers of 4-amino- and 4-aminomethyl-substituted prolinol derivatives, respectively, was accomplished by chemo- and regioselective functional group transformations at the 2- and 4-positions of the pyrrolidine moiety. These building blocks were used as valuable precursors for the preparation of new methoxybenzamide derivatives. Dopamine and serotonin binding studies involving the subtypes D1, D2(long), D2(short), D3 and D4 as well as 5-HT1(A) and 5-HT2 respectively, displayed interesting structure activity relationships, especially with respect to the absolute and relative configuration of the test compounds. As a complement to the D3 receptor preferring aminomethylpyrrolidine FAUC 21. the (2R,4R)-aminoprolinol derivative ent-24 (FAUC 65) preferentially recognizing the D4 subtype was developed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.019

文献信息

• Ex-chiral pool synthesis and receptor binding studies of 4-substituted prolinol derivatives
  作者：Cornelia Heindl、Harald Hübner、Peter Gmeiner

  DOI：10.1016/j.tetasy.2003.08.019

  日期：2003.10

  Starting from natural 4-hydroxyproline, preparation of the four possible stereoisomers of 4-amino- and 4-aminomethyl-substituted prolinol derivatives, respectively, was accomplished by chemo- and regioselective functional group transformations at the 2- and 4-positions of the pyrrolidine moiety. These building blocks were used as valuable precursors for the preparation of new methoxybenzamide derivatives. Dopamine and serotonin binding studies involving the subtypes D1, D2(long), D2(short), D3 and D4 as well as 5-HT1(A) and 5-HT2 respectively, displayed interesting structure activity relationships, especially with respect to the absolute and relative configuration of the test compounds. As a complement to the D3 receptor preferring aminomethylpyrrolidine FAUC 21. the (2R,4R)-aminoprolinol derivative ent-24 (FAUC 65) preferentially recognizing the D4 subtype was developed. (C) 2003 Elsevier Ltd. All rights reserved.