2,3,5-tri-O-benzyl-D-ribose oxime | 213617-00-6

• 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-D-ribose oxime
• 英文别名: (2R,3R,4S)-5-hydroxyimino-1,3,4-tris(phenylmethoxy)pentan-2-ol
• CAS: 213617-00-6
• 化学式: C₂₆H₂₉NO₅
• 分子量: 435.52
• InChiKey: AILMEHKZYKDQPG-UODIDJSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  80.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzyl-D-ribose oxime 在 吡啶 、 咪唑 、 四丁基氟化铵 、 碘 、 三苯基膦 作用下， 以 甲苯 、 苯 为溶剂， 反应 16.0h， 生成 (1S,2R,6S,9R,10R,11S)-4-benzyl-10,11-bis(phenylmethoxy)-9-(phenylmethoxymethyl)-7-oxa-4,8-diazatricyclo[6.3.0.02,6]undecane-3,5-dione
  参考文献：
  名称：

  Holzapfel, Cedric W.; Crous, Renier, Heterocycles, 1998, vol. 48, # 7, p. 1337 - 1342

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,5-三-O-(苯基甲基)-D-呋喃核糖 在 吡啶 、 盐酸羟胺 作用下， 反应 3.0h， 以95%的产率得到2,3,5-tri-O-benzyl-D-ribose oxime
  参考文献：
  名称：

  Holzapfel, Cedric W.; Crous, Renier, Heterocycles, 1998, vol. 48, # 7, p. 1337 - 1342

  摘要：

  DOI：

文献信息

• Reductive Cyclization of δ-Hydroxy Nitriles:  A New Synthesis of Glycosylamines
  作者：Andrew D. Dorsey、Jennifer E. Barbarow、Dirk Trauner

  DOI：10.1021/ol035111s

  日期：2003.9.1

  [reaction: see text] The stereoselective cyclization of delta-hydroxy nitriles to afford N,O-acetals and the application of this reaction toward the synthesis of glycosylamines is described.

  [反应：见正文]描述了δ-羟基腈的立体选择性环化以提供N，O-乙缩醛，以及该反应在糖胺合成中的应用。
• Spirocyclopropyl pyrrolidines as a new series of α-l-fucosidase inhibitors
  作者：Christophe Laroche、Jean-Bernard Behr、Jan Szymoniak、Philippe Bertus、Catherine Schütz、Pierre Vogel、Richard Plantier-Royon

  DOI：10.1016/j.bmc.2006.02.005

  日期：2006.6

  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.
• A convenient approach toward the synthesis of enantiopure isomers of DMDP and ADMDP
  作者：En-Lun Tsou、Yao-Ting Yeh、Pi-Hui Liang、Wei-Chieh Cheng

  DOI：10.1016/j.tet.2008.10.096

  日期：2009.1

  A practical method for the synthesis of five-membered iminocyclitols, pyrrolidine alkaloids bearing multiple hydroxyl substituents, has been developed. All of the eight key intermediates, enantiopure tri-O-benzyl cyclic nitrones, are prepared from four cheap, readily available D-aldopentoses. The nucleophilic addition of cyclic nitrones with vinyl magnesium chloride and TMSCN shows high 2,3-trans stereoselectivity. To construct the 2,3-cis configurations, inversion of the C-2 nitrile group is achieved via an elimination-reduction sequence. Using this approach, five isomers of DMDP and six isomers of ADMDP are prepared efficiently. In the biological evaluation, iminocyclitol 27 is a new and potent inhibitor against beta-hexosaminidase with an IC50 value of 0.2 mu M. (C) 2008 Elsevier Ltd. All rights reserved.