3-deoxy-3-C-(pyrene-1-yl-aminomethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose | 735311-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 3-deoxy-3-C-(pyrene-1-yl-aminomethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
• CAS: 735311-28-1
• 化学式: C₂₉H₃₁NO₅
• 分子量: 473.569
• InChiKey: MGCKFWXZKFYQNP-NFKNIIAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  58.18
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-deoxy-3-C-(pyrene-1-yl-aminomethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以29%的产率得到(1S,3R,4S,5R,8R)-3-hydroxymethyl-7-pyren-1-yl-2-oxa-7-aza-bicyclo[3.2.1]octane-4,8-diol
  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 3-deoxy-3-C-(pyrene-1-yl-aminomethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
  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