tert-butyl (2S,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-[(2S)-5-oxooxolan-2-yl]pyrrolidine-1-carboxylate | 181705-84-0

• 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: tert-butyl (2S,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-[(2S)-5-oxooxolan-2-yl]pyrrolidine-1-carboxylate
• CAS: 181705-84-0
• 化学式: C₃₀H₄₁NO₅Si
• 分子量: 523.745
• InChiKey: UVXOEBWXAVOCOS-HRNNMHKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-[(2S)-5-oxooxolan-2-yl]pyrrolidine-1-carboxylate 在 B-溴代邻苯二氧硼烷 、 sodium methylate 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 (3S,8S,9R)-3-(tert-butyldiphenylsilanyloxymethyl)-8-methoxyhexahydroindolizin-5-one
  参考文献：
  名称：

  Exploring the chiral space within the active site of α-thrombin with a constrained mimic of d -Phe-Pro-Arg — design, synthesis, inhibitory activity, and X-ray structure of an enzyme–inhibitor complex

  摘要：

  An indolizidinone motif with strategically placed substitutents was designed and synthesized as a constrained mimic of D-Phe-Pro-Arg. Low nanomolar inhibition of a-thrombin validates the design elements in this inhibitor which also exhibits a 20-fold selectivity for thrombin versus trypsin. An X-ray crystal structure of the inhibitor with alpha-thrombin shows the expected interactions with key amino acids within the active site and some notable changes in positions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00669-1
• 作为产物：
  描述：

  N-tert-butyloxycarbonyl(5-diphenyl-tert-butylsilyloxymethyl)-2-hydroxypyrrolidine 在 palladium on activated charcoal 三氟化硼乙醚 、 叔丁基二甲硅基三氟甲磺酸酯 、 氢气 、 sodium acetate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 tert-butyl (2S,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-[(2S)-5-oxooxolan-2-yl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Lewis Acid Assisted Vinylogous Mannich and Mukaiyama Aldol Reactions: A Route to Densely Hydroxylated Indolizidine Alkaloid Analogues

  摘要：

  The hydroxymethyl-substituted indolizidines 6 and 7, representative members of a ring-B-expanded alexine- australine subclass, are readily accessible by starting with furan-based silyloxydiene 12 and hydroxymethyl hemiaminal 11, through a synthesis sequence involving a scantily exploited vinylogous version of the Mannich reaction. The key iminium electrophilic acceptor 11 is, in turn, available through a vinylogous intermolecular Mukaiyama aldolization process between pyrrole-based silyloxydiene 8 and (S)-glyceraldehyde 9.

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1395::aid-ejoc1395>3.0.co;2-t