(S)-(+)-N-tert-butyloxycarbonyl-5-(triisopropylsilyloxymethyl)pyrrolid-3-en-2-one | 222307-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (S)-(+)-N-tert-butyloxycarbonyl-5-(triisopropylsilyloxymethyl)pyrrolid-3-en-2-one
• 英文别名: tert-butyl (2S)-5-oxo-2-[tri(propan-2-yl)silyloxymethyl]-2H-pyrrole-1-carboxylate
• CAS: 222307-12-2
• 化学式: C₁₉H₃₅NO₄Si
• 分子量: 369.577
• InChiKey: VERZFVNMRCRKNH-INIZCTEOSA-N

物化性质

• 沸点：
  393.7±44.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  (S)-(+)-N-tert-butyloxycarbonyl-5-(triisopropylsilyloxymethyl)pyrrolid-3-en-2-one 在 二苯甲酮 、 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成 (4S,5S)-(+)-N-tert-butyloxycarbonyl-4-fluoromethyl-5-(triisopropylsilyloxymethyl) pyrrolidin-2-one
  参考文献：
  名称：

  Photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one: A new route to 4(S), 5(S)-disubstituted pyrrolidin-2-ones

  摘要：

  We describe the photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one to produce 5(S)-triisopropylsiloxymethyl-4( S)-hydroxymethylpyrrolidine-2-one, and conversion of this into a variety of 4( S), S(S)-pyrrolidine-2-ones. Photoinduced addition of methanol to 5(R)-N-boc-5-amino-dihydropyran-2(5H)-one yielded the unexpected product 4(S)-1'-[2'-hydroxy, 1'-( R)-N-boc-amino]ethyl-tetrahydrofuran-2-one via rearrangement of the initial photoadduct. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01094-1
• 作为产物：
  描述：

  L-焦谷氨酸甲酯 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-(+)-N-tert-butyloxycarbonyl-5-(triisopropylsilyloxymethyl)pyrrolid-3-en-2-one
  参考文献：
  名称：

  A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal

  摘要：

  Details of the evolution of a synthetic strategy toward the spirocyclic chlorocyclopentane core of oroidin-derived alkaloids, including the axinellamines and potentially adaptable to palau'amine, are described. A proposed refinement of the Kinnel-Scheuer biosynthetic proposal for palau'amine is posited. Studies undertaken to improve the regioselectivity and efficiency of a key Diels-Alder reaction utilizing a novel protecting group strategy, microwave chemistry, and other strategies are described. Further insights regarding the suitability of different protecting groups during the epoxidation/chlorination/ring contraction sequence are disclosed. Several interesting by-products from this reaction sequence are reported. These studies have led to a unified synthetic strategy to the axinellamines and palau'amine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.068

文献信息

• [EN] HCV PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PROTÉASE DU VHC
  申请人：SEQUOIA PHARMACEUTICALS INC

  公开号：WO2010021717A3

  公开（公告）日：2010-04-15
• A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal
  作者：Paul J. Dransfield、Anja S. Dilley、Shaohui Wang、Daniel Romo

  DOI：10.1016/j.tet.2005.12.068

  日期：2006.5

  Details of the evolution of a synthetic strategy toward the spirocyclic chlorocyclopentane core of oroidin-derived alkaloids, including the axinellamines and potentially adaptable to palau'amine, are described. A proposed refinement of the Kinnel-Scheuer biosynthetic proposal for palau'amine is posited. Studies undertaken to improve the regioselectivity and efficiency of a key Diels-Alder reaction utilizing a novel protecting group strategy, microwave chemistry, and other strategies are described. Further insights regarding the suitability of different protecting groups during the epoxidation/chlorination/ring contraction sequence are disclosed. Several interesting by-products from this reaction sequence are reported. These studies have led to a unified synthetic strategy to the axinellamines and palau'amine. (c) 2006 Elsevier Ltd. All rights reserved.
• Photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one: A new route to 4(S), 5(S)-disubstituted pyrrolidin-2-ones
  作者：Michael G.B. Drew、R.John Harrison、John Mann、Allen J. Tench、Robert J. Young

  DOI：10.1016/s0040-4020(98)01094-1

  日期：1999.1

  We describe the photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one to produce 5(S)-triisopropylsiloxymethyl-4( S)-hydroxymethylpyrrolidine-2-one, and conversion of this into a variety of 4( S), S(S)-pyrrolidine-2-ones. Photoinduced addition of methanol to 5(R)-N-boc-5-amino-dihydropyran-2(5H)-one yielded the unexpected product 4(S)-1'-[2'-hydroxy, 1'-( R)-N-boc-amino]ethyl-tetrahydrofuran-2-one via rearrangement of the initial photoadduct. (C) 1999 Elsevier Science Ltd. All rights reserved.