(3R,4R,5S)-(5-hydroxymethyl-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-yl)carbamic acid benzyl ester | 852063-51-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R,4R,5S)-(5-hydroxymethyl-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-yl)carbamic acid benzyl ester
• CAS: 852063-51-5
• 化学式: C₂₁H₂₀N₂O₅
• 分子量: 380.4
• InChiKey: MOIZBDPDYQXFKG-CEXWTWQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  100.65
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3R,4R,5S)-(5-hydroxymethyl-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-yl)carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以80%的产率得到(3R,4R,5S)-(3-amino-4-(1H-indol-3-yl)-5-hydroxymethyl)-4,5-dihydrofuran-2(3H)-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：

  (3S,4S,5S)-5-hydroxymethyl-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-carboxylic acid 在 咪唑 、 二苯基磷酸 、 水 、 溶剂黄146 、 三乙胺 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 64.0h， 生成 (3R,4R,5S)-(5-hydroxymethyl-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-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

• 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.