(2S,3R)-N-tert-butyloxycarbonyl-3-(tert-butyldimethylsilyloxy)-2-formylpyrrolidine | 627531-58-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,3R)-N-tert-butyloxycarbonyl-3-(tert-butyldimethylsilyloxy)-2-formylpyrrolidine
• 英文别名: (2S,3R)-3-(tert-butyldimethylsilanyloxy)-2-formylpyrrolidine-1-carboxylic acid tert-butyl ester；tert-butyl (2S,3R)-3-tert-butyldimethylsilyloxy-2-formyl-pyrrolidine-1-carboxylate；tert-Butyl-(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-formylpyrrolidine-1-carboxylate；tert-butyl (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-formylpyrrolidine-1-carboxylate
• CAS: 627531-58-2
• 化学式: C₁₆H₃₁NO₄Si
• 分子量: 329.512
• InChiKey: KAPDAIYAVGIGQG-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R)-N-tert-butyloxycarbonyl-3-(tert-butyldimethylsilyloxy)-2-formylpyrrolidine 在 正丁基锂 、 醋酸叔丁酯 、 3 A molecular sieve 、 四丁基氟化铵 、 对甲苯磺酸 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 为溶剂， 反应 3.83h， 生成 tert-Butyl <4S-(4α,4aα,7aα)>-5-(tert-Butoxycarbonyl)-hexahydro-2,2-dimethyl-1,3-dioxino<5,4-b>pyrrole-4-acetate
  参考文献：
  名称：

  Asymmetric intramolecular amidation of N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine. A new entry to chiral building blocks for the synthesis of biologically active nitrogen-containing compounds

  摘要：

  Sharpless reaction of racemic N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine (1) leads to both an asymmetric kinetic resolution to provide optically active 1, which was subsequently used for intramolecular amidomercuration, and asymmetric epoxidation followed by concomitant cyclization into optically active cis-3-hydroxy-2-(hydroxymethyl)pyrrolidine (3). Optically active 1 and 3 have been expediently used as chiral building blocks in the asymmetric synthesis of several biologically active natural products.

  DOI：

  10.1021/jo00001a045
• 作为产物：
  描述：

  1-(N-tert-Butyloxycarbonylamino)-3-(t-butyldimethylsilyloxy)-4-oxiranyl pentane 在 三氟化硼乙醚 、 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 1.78h， 生成 (2S,3R)-N-tert-butyloxycarbonyl-3-(tert-butyldimethylsilyloxy)-2-formylpyrrolidine
  参考文献：
  名称：

  排毒复合物的合成研究。I。（-）排毒素的全合成

  摘要：

  据报道，共合成了排毒复合物的母体氨基酸（-）排毒素（1）。已开发出两种通往关键中间体8a的不同途径：一种途径来自无环前体，另一种途径来自L-脯氨酸。对8a至1的修饰采用了立体选择性醛醇缩合。

  DOI：

  10.1016/0040-4020(86)80005-9
• 作为试剂：
  描述：

  二甲基亚砜 、 草酰氯 、 (2S,3R)-N-tert-butyloxycarbonyl-3-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidine 、 三乙胺 在 Acetone cardice 、 水 、 二氯甲烷 、 Brine 、 magnesium sulfate 、 (2S,3R)-N-tert-butyloxycarbonyl-3-(tert-butyldimethylsilyloxy)-2-formylpyrrolidine 、 乙酸乙酯 、 hexanes 作用下， 以 二氯甲烷 为溶剂， 反应 17.83h， 以afforded the desired aldehyde (4), 2.03 g in 87% yield的产率得到(2S,3R)-N-tert-butyloxycarbonyl-3-(tert-butyldimethylsilyloxy)-2-formylpyrrolidine
  参考文献：
  名称：

  ANTIBACTERIAL FLUOROQUINOLONE ANALOGS

  摘要：

  本发明公开了具有抗菌活性的化合物。该化合物具有以下结构（I）：包括立体异构体、药学上可接受的盐和前药，其中A、B、D、E、G、R1、R2、R3、R4、R5、R6和R7如本文所定义。本发明还公开了与制备和使用这种化合物相关的方法，以及包含这种化合物的制药组合物。

  公开号：

  US20120058989A1

文献信息

• Bicyclic modulators of androgen receptor function
  申请人：Nirschl Alexandra

  公开号：US20050197359A1

  公开（公告）日：2005-09-08

  The present invention relates to bicyclic compounds according to formula I, pharmaceutical compositions containing such compounds and methods of using such compounds in the treatment of androgen receptor-associated conditions, such as age-related diseases, for example sarcopenia, wherein R 1 , R 2 , R 5 , X, Y and n are defined herein.

  本发明涉及按照式I的双环化合物，包含这种化合物的药物组合物以及使用这种化合物治疗与雄激素受体相关疾病的方法，例如与年龄相关的疾病，例如肌少症，其中R1、R2、R5、X、Y和n在此处定义。
• BICYCLIC MODULATORS OF ANDROGEN RECEPTOR FUNCTION
  申请人：Sun Chong-Qing

  公开号：US20080108649A1

  公开（公告）日：2008-05-08

  There are provided compounds according to formula I wherein the substitutents are as described herein. Further provided are methods of using such compounds for the treatment of nuclear hormone receptor-associated conditions, such as age related diseases, for example sarcopenia. Also provided are pharmaceutical compositions containing such compounds and processes for preparing some of the compounds of the invention. Other embodiments are also disclosed.

  提供了按公式I描述的化合物，其中取代基如此描述。还提供了使用这种化合物治疗核激素受体相关疾病的方法，例如与年龄相关的疾病，例如肌肉萎缩症。还提供了含有这种化合物的药物组合物和制备本发明部分化合物的方法。还揭示了其他实施例。
• [EN] ANTIBACTERIAL FLUOROQUINOLONE ANALOGS<br/>[FR] ANALOGUES DE FLUOROQUINOLONES ANTIBACTÉRIENS
  申请人：ACHAOGEN INC

  公开号：WO2009137130A3

  公开（公告）日：2010-01-21
• Discovery of Potent and Muscle Selective Androgen Receptor Modulators through Scaffold Modifications
  作者：James J. Li、James C. Sutton、Alexandra Nirschl、Yan Zou、Haixia Wang、Chongqing Sun、Zulan Pi、Rebecca Johnson、Stanley R. Krystek,、Ramakrishna Seethala、Rajasree Golla、Paul G. Sleph、Blake C. Beehler、Gary J. Grover、Aberra Fura、Viral P. Vyas、Cindy Y. Li、Jack Z. Gougoutas、Michael A. Galella、Robert Zahler、Jacek Ostrowski、Lawrence G. Hamann

  DOI：10.1021/jm070312d

  日期：2007.6.1

  A novel series of imidazolin-2-ones were designed and synthesized as highly potent, orally active and muscle selective androgen receptor modulators (SARMs), with most of the compounds exhibiting low nM in vitro potency in androgen receptor (AR) binding and functional assays. Once daily oral treatment with the lead compound 11a (AR K-i = 0.9 nM, EC50 = 1.8 nM) for 14 days induced muscle growth with an ED50 of 0.09 mg/kg, providing approximately 50-fold selectivity over prostate growth in an orchidectomized rat model. Pharmacokinetic studies in rats demonstrated that the lead compound 11a had oral bioavailability of 65% and a plasma half-life of 5.5 h. On the basis of their preclinical profiles, the SARMs in this series are expected to provide beneficial anabolic effects on muscle with minimal androgenic effects on prostate tissue.
• <i>N</i>-Aryl-oxazolidin-2-imine Muscle Selective Androgen Receptor Modulators Enhance Potency through Pharmacophore Reorientation
  作者：Alexandra A. Nirschl、Yan Zou、Stanley R. Krystek、James C. Sutton、Ligaya M. Simpkins、John A. Lupisella、Joyce E. Kuhns、Ramakrishna Seethala、Rajasree Golla、Paul G. Sleph、Blake C. Beehler、Gary J. Grover、Donald Egan、Aberra Fura、Viral P. Vyas、Yi-Xin Li、John S. Sack、Kevin F. Kish、Yongmi An、James A. Bryson、Jack Z. Gougoutas、John DiMarco、Robert Zahler、Jacek Ostrowski、Lawrence G. Hamann

  DOI：10.1021/jm801583j

  日期：2009.5.14

  A novel selective androgen receptor modulator (SARM) scaffold was discovered as a byproduct obtained during synthesis of our earlier series of imidazolidin-2-ones. The resulting oxazolidin-2-imines are among the most potent SARMs known, with many analogues exhibiting sub-nM in vitro potency in binding and functional assays. Despite the potential for hydrolytic instability at gut pH, compounds of the present class showed good oral bioavailability and were highly active in a standard rodent pharmacological model.