(3S,4R,5R)-[5-(tertbutyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxopyrrolidin-3-yl]carbamic acid benzyl ester | 505086-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3S,4R,5R)-[5-(tertbutyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxopyrrolidin-3-yl]carbamic acid benzyl ester
• CAS: 505086-85-1
• 化学式: C₂₇H₃₅N₃O₄Si
• 分子量: 493.678
• InChiKey: HEZKNLFADFIWOK-VXNXHJTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  92.45
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R)-[5-(tertbutyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxopyrrolidin-3-yl]carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 31.0h， 以97%的产率得到(3S,4S,5R)-[3-amino-5-(tertbutyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)]pyrrolidin-2-one
  参考文献：
  名称：

  Diastereocontrolled multicomponent pathway to 3,4-heterocycle-annulated tetrahydro-β-carbolines

  摘要：

  A diastereoselective synthesis, using the Yonemitsu-type trimolecular condensation as the key step, has been used for the preparation of 3,4-heterocycle(furanone-, pyrrolidinone- and pyranone-) annulated tetrahydro-beta-carbolines. The chirality Of D-glyceraldehyde or that of the Garner's aldehyde ensured a high and predictable diastereocontrol of the additional newly created stereocentres. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.008
• 作为产物：
  描述：

  (3R,4R,5R)-5-tert-butoxycarbonylamino-4-(1H-indol-3-yl)-2-oxotetrahydropyran-3-carboxylic acid methyl ester 在 咪唑 、 氢氧化钾 、 二苯基磷酸 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 30.0h， 生成 (3S,4R,5R)-[5-(tertbutyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxopyrrolidin-3-yl]carbamic acid benzyl ester
  参考文献：
  名称：

  Diastereocontrolled multicomponent pathway to 3,4-heterocycle-annulated tetrahydro-β-carbolines

  摘要：

  A diastereoselective synthesis, using the Yonemitsu-type trimolecular condensation as the key step, has been used for the preparation of 3,4-heterocycle(furanone-, pyrrolidinone- and pyranone-) annulated tetrahydro-beta-carbolines. The chirality Of D-glyceraldehyde or that of the Garner's aldehyde ensured a high and predictable diastereocontrol of the additional newly created stereocentres. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.008

文献信息

• Synthesis of chiral 2′,3′-pyranone(pyrrolidinone)-fused tryptamines
  作者：Emmanuel Dardennes、Árpád Kovács-Kulyassa、Andrea Renzetti、Janos Sapi、Jean-Yves Laronze

  DOI：10.1016/s0040-4039(02)02537-6

  日期：2003.1

  Chiral pyrano- and pyrrolidino-fused tryptamines were prepared by a diasteroselective trimolecular condensation between indole, Garner's aldehyde and Meldrum's acid, followed by selective functional group transformations, (C) 2002 Elsevier Science Ltd. All rights reserved.
• Diastereocontrolled multicomponent pathway to 3,4-heterocycle-annulated tetrahydro-β-carbolines
  作者：Emmanuel Dardennes、Árpád Kovács-Kulyassa、Michel Boisbrun、Christian Petermann、Jean-Yves Laronze、Janos Sapi

  DOI：10.1016/j.tetasy.2005.02.008

  日期：2005.4

  A diastereoselective synthesis, using the Yonemitsu-type trimolecular condensation as the key step, has been used for the preparation of 3,4-heterocycle(furanone-, pyrrolidinone- and pyranone-) annulated tetrahydro-beta-carbolines. The chirality Of D-glyceraldehyde or that of the Garner's aldehyde ensured a high and predictable diastereocontrol of the additional newly created stereocentres. (c) 2005 Elsevier Ltd. All rights reserved.