(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidine-2-carbonitrile | 1105054-55-4

• 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: (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidine-2-carbonitrile
• CAS: 1105054-55-4
• 化学式: C₂₇H₂₈N₂O₃
• 分子量: 428.531
• InChiKey: YHUNYXUAKIZHJS-FPCALVHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.51
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidin-2-one 在 Schwartz's reagent 、 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.92h， 生成 (2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidine-2-carbonitrile 、 (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidine-2-carbonitrile
  参考文献：
  名称：

  Sugar-derived cyclic imines: one-pot synthesis and direct functionalization

  摘要：

  A simple method for the synthesis of sugar-derived imines by a Schwartz's reagent reduction of easily available sugar lactams has been described. A direct addition of nucleophiles to the generated in situ cyclic imines and subsequent deprotection of hydroxyl function allows to convert sugar lactams in polyhydroxylated pyrrolidines and piperidines. (C) 2014 Elsevier Ltd. All rights

  DOI：

  10.1016/j.tet.2014.01.039

文献信息

• A Convenient Approach towards the Synthesis of ADMDP Type Iminosugars and Nojirimycin Derivatives from Sugar-Derived Lactams
  作者：Piotr Szcześniak、Barbara Grzeszczyk、Bartłomiej Furman

  DOI：10.3390/molecules26185459

  日期：——

  An efficient method for the synthesis of nojirimycin- and pyrrolidine-based iminosugar derivatives has been developed. The strategy is based on the partial reduction in sugar-derived lactams by Schwartz’s reagent and tandem stereoselective nucleophilic addition of cyanide or a silyl enol ether dictated by Woerpel’s or diffusion control models, which affords amino-modified iminosugars, such as ADMDP

  已开发出一种合成野尻霉素和吡咯烷基亚氨基糖衍生物的有效方法。该策略基于 Schwartz 试剂部分还原糖衍生的内酰胺，以及 Woerpel 或扩散控制模型规定的氰化物或甲硅烷基烯醇醚的串联立体选择性亲核加成，提供氨基修饰的亚氨基糖，如 ADMDP 或更高的野尻霉素衍生物.
• A convenient approach toward the synthesis of enantiopure isomers of DMDP and ADMDP
  作者：En-Lun Tsou、Yao-Ting Yeh、Pi-Hui Liang、Wei-Chieh Cheng

  DOI：10.1016/j.tet.2008.10.096

  日期：2009.1

  A practical method for the synthesis of five-membered iminocyclitols, pyrrolidine alkaloids bearing multiple hydroxyl substituents, has been developed. All of the eight key intermediates, enantiopure tri-O-benzyl cyclic nitrones, are prepared from four cheap, readily available D-aldopentoses. The nucleophilic addition of cyclic nitrones with vinyl magnesium chloride and TMSCN shows high 2,3-trans stereoselectivity. To construct the 2,3-cis configurations, inversion of the C-2 nitrile group is achieved via an elimination-reduction sequence. Using this approach, five isomers of DMDP and six isomers of ADMDP are prepared efficiently. In the biological evaluation, iminocyclitol 27 is a new and potent inhibitor against beta-hexosaminidase with an IC50 value of 0.2 mu M. (C) 2008 Elsevier Ltd. All rights reserved.