2,3,5-tri-O-benzyl-4-O-methanesulfonyl-L-xylononitrile | 897048-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,5-tri-O-benzyl-4-O-methanesulfonyl-L-xylononitrile
• 英文别名: [(2S,3S,4R)-4-cyano-1,3,4-tris(phenylmethoxy)butan-2-yl] methanesulfonate
• CAS: 897048-81-6
• 化学式: C₂₇H₂₉NO₆S
• 分子量: 495.596
• InChiKey: XBWJJECDNWLMDT-PVHODMMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzyl-4-O-methanesulfonyl-L-xylononitrile 在 palladium on activated charcoal titanium(IV) isopropylate 、 盐酸 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 6.0h， 生成 (5R,6R,7R)-6,7-Dihydroxy-5-hydroxymethyl-4-aza-spiro[2.4]heptane-4-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Spirocyclopropyl pyrrolidines as a new series of α-l-fucosidase inhibitors

  摘要：

  Polyhydroxy 4-azaspiro[2.4]heptane derivatives (spirocyclopropyl iminosugars) were prepared in four to six steps from readily available protected aldoses. The key step of the reaction sequence involves a titanium-mediated aminocyclopropanation of glycononitriles with subsequent cyclization. Five new polyhydroxypyrrolidines so-obtained have been evaluated for their ability to inhibit 16 glycosidases. One of them exhibits selective inhibition Of alpha-L-fucosidase from bovine kidney (K-i = 1.6 mu M, competitive). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.005
• 作为产物：
  描述：

  2,3,5-tri-O-benzyl-L-xylofuranose 在 吡啶 、 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 2,3,5-tri-O-benzyl-4-O-methanesulfonyl-L-xylononitrile
  参考文献：
  名称：

  Spirocyclopropyl pyrrolidines as a new series of α-l-fucosidase inhibitors

  摘要：

  Polyhydroxy 4-azaspiro[2.4]heptane derivatives (spirocyclopropyl iminosugars) were prepared in four to six steps from readily available protected aldoses. The key step of the reaction sequence involves a titanium-mediated aminocyclopropanation of glycononitriles with subsequent cyclization. Five new polyhydroxypyrrolidines so-obtained have been evaluated for their ability to inhibit 16 glycosidases. One of them exhibits selective inhibition Of alpha-L-fucosidase from bovine kidney (K-i = 1.6 mu M, competitive). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.005

文献信息

• Tandem Nucleophilic Addition/Cyclization Reaction in the Synthesis of Ketimine-Type Iminosugars
  作者：Jean-Bernard Behr、Adel Kalla、Dominique Harakat、Richard Plantier-Royon

  DOI：10.1021/jo702616x

  日期：2008.5.1

  unsaturated iminosugars has not yet been extensively studied because of a lack of general synthetic methods. A practical synthesis of these cyclic ketimine sugars was developed, which was based on a tandem addition−cyclization reaction of a Grignard reagent to a ω-methanesulfonylglycononitrile.

  由于缺乏通用的合成方法，不饱和亚氨基糖的生物活性尚未得到广泛的研究。这些环酮亚胺糖的实用合成方法是基于格氏试剂与ω-甲磺酰基甘氨腈的串联加成-环化反应而开发的。