N-(pyren-1-yl)-(3R,4S)-4-[(1S,2R)-1,2,3-trihydroxypropyl]pyrrolidin-3-ol | 735311-27-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N-(pyren-1-yl)-(3R,4S)-4-[(1S,2R)-1,2,3-trihydroxypropyl]pyrrolidin-3-ol
• 英文别名: (1S,2R)-1-[(3S,4R)-4-hydroxy-1-pyren-1-ylpyrrolidin-3-yl]propane-1,2,3-triol
• CAS: 735311-27-0
• 化学式: C₂₃H₂₃NO₄
• 分子量: 377.44
• InChiKey: DTQCYCKQEKTGJE-YPIYEQTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(pyren-1-yl)-(3R,4S)-4-[(1S,2R)-1,2,3-trihydroxypropyl]pyrrolidin-3-ol 在 sodium periodate 、 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以76%的产率得到(3R,4S)-1-(pyren-1-yl)-4-[(1S)-1,2-dihydroxyethyl]pyrrolidin-3-ol
  参考文献：
  名称：

  Facile route for the synthesis of the iminosugar nucleoside (3R,4R)-1-(pyren-1-yl)-4-(hydroxymethyl)pyrrolidin-3-ol

  摘要：

  N-(Pyren-1-yl)-(3R,4S)-4-[(1S,2R)-1,2,3-trihydroxypropyl]pyrrolidin-3-ol (4) was obtained in 36% yield from 3-deoxy-3-C-formyl-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose (3) by combined hydrolysis and aminoalkylation reactions with 1-aminopyrene in a one-pot reaction. Cleavage reactions of the exocyclic triol chain in 4 with NaIO4 and NaBH4 resulted in iminosugars 7 and 8, which are analogues of the faranose forms of 2-deoxy-D-allose and of 2-deOXY-D-ribose, the latter analogue N-(pyren-1-yl)(3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol (8) being formed in 83% yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.03.022
• 作为产物：
  描述：

  ((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-(pyren-1-yl)-(3R,4S)-4-[(1S,2R)-1,2,3-trihydroxypropyl]pyrrolidin-3-ol
  参考文献：
  名称：

  Facile route for the synthesis of the iminosugar nucleoside (3R,4R)-1-(pyren-1-yl)-4-(hydroxymethyl)pyrrolidin-3-ol

  摘要：

  N-(Pyren-1-yl)-(3R,4S)-4-[(1S,2R)-1,2,3-trihydroxypropyl]pyrrolidin-3-ol (4) was obtained in 36% yield from 3-deoxy-3-C-formyl-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose (3) by combined hydrolysis and aminoalkylation reactions with 1-aminopyrene in a one-pot reaction. Cleavage reactions of the exocyclic triol chain in 4 with NaIO4 and NaBH4 resulted in iminosugars 7 and 8, which are analogues of the faranose forms of 2-deoxy-D-allose and of 2-deOXY-D-ribose, the latter analogue N-(pyren-1-yl)(3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol (8) being formed in 83% yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.03.022

文献信息

• Facile route for the synthesis of the iminosugar nucleoside (3R,4R)-1-(pyren-1-yl)-4-(hydroxymethyl)pyrrolidin-3-ol
  作者：Allam A Hassan、Per T Jørgensen、Paul C Stein、M.E Abdel Fattah、Ibrahim I.A El Gawad、Erik B Pedersen

  DOI：10.1016/j.carres.2004.03.022

  日期：2004.6

  N-(Pyren-1-yl)-(3R,4S)-4-[(1S,2R)-1,2,3-trihydroxypropyl]pyrrolidin-3-ol (4) was obtained in 36% yield from 3-deoxy-3-C-formyl-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose (3) by combined hydrolysis and aminoalkylation reactions with 1-aminopyrene in a one-pot reaction. Cleavage reactions of the exocyclic triol chain in 4 with NaIO4 and NaBH4 resulted in iminosugars 7 and 8, which are analogues of the faranose forms of 2-deoxy-D-allose and of 2-deOXY-D-ribose, the latter analogue N-(pyren-1-yl)(3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol (8) being formed in 83% yield. (C) 2004 Elsevier Ltd. All rights reserved.