(5S,2'S,5'S)-5-[5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'yl]-tetrahydrofuran-2-one | 181705-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (5S,2'S,5'S)-5-[5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'yl]-tetrahydrofuran-2-one
• 英文别名: (5S)-5-[(2S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]pyrrolidin-2-yl]oxolan-2-one
• CAS: 181705-71-5
• 化学式: C₂₅H₃₃NO₃Si
• 分子量: 423.627
• InChiKey: WVISTDCCABAVBD-VJBMBRPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S,2'S,5'S)-5-[5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'yl]-tetrahydrofuran-2-one 在 sodium methylate 、 silver(l) oxide 作用下， 以 甲醇 、 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 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 叔丁基二甲硅基三氟甲磺酸酯 、 氢气 、 sodium acetate 、 苯硫酚 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 (5S,2'S,5'S)-5-[5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'yl]-tetrahydrofuran-2-one
  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

文献信息

• A versatile synthesis of a β-turn peptidomimetic scaffold: An approach towards a designed model antagonist of the tachykinin NK-2 receptor
  作者：Stephen Hanessian、Grant McNaughton-Smith

  DOI：10.1016/s0960-894x(96)00275-2

  日期：1996.7

  A general and stereocontrolled synthesis of an azabicyclo[4.3.0] nonane amino acid template with an appended substitutent at C-5 was developed The approach allows for stereochemical and functional variations that extend the utility of these rigid amino acid motifs as peptidomimetics. The synthesis of a weakly active but specific NK-2 receptor antagonist is described. Copyright (C) 1996 Elsevier Science Ltd
• Lewis Acid Assisted Vinylogous Mannich and Mukaiyama Aldol Reactions: A Route to Densely Hydroxylated Indolizidine Alkaloid Analogues
  作者：Gloria Rassu、Paola Carta、Luigi Pinna、Lucia Battistini、Franca Zanardi、Domenico Acquotti、Giovanni Casiraghi

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

  日期：1999.6

  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.
• 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
  作者：Stephen Hanessian、Elise Balaux、Djorde Musil、Lise-Lotte Olsson、Ingemar Nilsson

  DOI：10.1016/s0960-894x(99)00669-1

  日期：2000.2

  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.