2,3,5,-tri-O-benzyl-D-arabinose-O-[(tert-butyl)diphenylsilyl]oxime | 537030-20-9

• 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-arabinose-O-[(tert-butyl)diphenylsilyl]oxime
• 英文别名: (2R,3R,4R)-2,3,5-tris(benzyloxy)-4-hydroxypentanal O-(tertbutyldiphenylsilyl)oxime
• CAS: 537030-20-9
• 化学式: C₄₂H₄₇NO₅Si
• 分子量: 673.924
• InChiKey: DJMYJJPQXJIDNB-MHEUVVKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  49.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  69.51
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,3,5,-tri-O-benzyl-D-arabinose-O-[(tert-butyl)diphenylsilyl]oxime 在 咪唑 、 四丁基氟化铵 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 30.5h， 生成 (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1-hydroxypyrrolidine-2-carbonitrile
  参考文献：
  名称：

  通过原位筛选单价和二价吡咯烷亚氨基糖文库发现人氨基己糖苷酶抑制剂

  摘要：

  由各自的叠氮基/氨基己基吡咯烷亚氨基糖前体通过 CuAAC 和 (硫代) 脲键形成反应合成了两个单体和二聚吡咯烷亚氨基糖库。筛选所得的单体和二聚体化合物对来自杰克豆的β- N-乙酰氨基葡萄糖苷酶的抑制作用，杰克豆是人类溶酶体氨基己糖苷酶的植物直系同源物。然后针对人溶酶体 β- N-乙酰氨基己糖苷酶 B (hHexB) 和人核质 β- N-乙酰氨基葡萄糖苷酶 (hOGA) 评估这些文库的最佳抑制剂的选择。该评估确定了一种有效 (nM) 和选择性的 hOGA 单体抑制剂（化合物7A) 对这种酶的亲和力比对 hHexB 的亲和力高 6890 倍。相应的二聚体衍生物（化合物9D）进一步显着提高了抑制 hOGA 的选择性（对 hOGA 的选择性比 hHexB 高 2.7×10 4倍）和抑制效力（一个数量级）。进行对接研究以解释在化合物7A中观察到的抑制选择性。

  DOI：

  10.1016/j.bioorg.2022.105650
• 作为产物：
  描述：

  2,3,5-三-O-(苯基甲基)-D-呋喃阿拉伯糖 在 吡啶 、 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 2,3,5,-tri-O-benzyl-D-arabinose-O-[(tert-butyl)diphenylsilyl]oxime
  参考文献：
  名称：

  7-脱氧木麻黄碱的合成及糖苷酶抑制活性

  摘要：

  1,4-脱水-2,3,5-三-O-苄基-1-脱氧-1-亚氨基-D-阿拉伯糖醇N-氧化物（8）与烯丙醇的反应生成两种吡咯并的3.6：1混合物[1,2- b ]异恶唑衍生物13和14。主要的加合物13被转化为7-脱氧木麻黄碱（7），这是一种来自根霉菌的强力，特异性和竞争性淀粉葡糖苷酶抑制剂（见表）。

  DOI：

  10.1002/hlca.200390248

文献信息

• Cycloadditions of Sugar-Derived ­Nitrones Targeting Polyhydroxylated Indolizidines
  作者：Daniele Martella、Giampiero D'Adamio、Camilla Parmeggiani、Francesca Cardona、Elena Moreno-Clavijo、Inmaculada Robina、Andrea Goti

  DOI：10.1002/ejoc.201501427

  日期：2016.3

  transformation of the reaction products allowed the synthesis of four new tetrahydroxylated indolizidines. Their activity as glycosidase inhibitors was evaluated against a panel of commercially available glycosidases. The specificity of inhibitory activity against amyloglucosidase and α-mannosidases depends on the configuration at C-2 of the indolizidine moiety.

  报道了三种戊糖衍生的吡咯啉 N-氧化物与单和双取代烯烃的 1,3 偶极环加成反应。观察到环加成的非对映选择性强烈依赖于硝酮立体中心的相对构型。反应产物的进一步转化允许合成四种新的四羟基化吲哚里西啶。它们作为糖苷酶抑制剂的活性是针对一组可商购的糖苷酶进行评估的。对淀粉葡萄糖苷酶和 α-甘露糖苷酶的抑制活性的特异性取决于吲哚里西啶部分 C-2 处的构型。
• Regiospecific formation of sugar-derived ketonitrone towards unconventional <i>C</i>-branched pyrrolizidines and indolizidines
  作者：Fabien Massicot、Gatien Messire、Alexis Vallée、Jean-Luc Vasse、Sandrine Py、Jean-Bernard Behr

  DOI：10.1039/c9ob01419e

  日期：——

  The synthesis of unprecedented branched pyrrolizidines and indolizidines was accomplished via nitrone chemistry. The required ketonitrone, a known intermediate usually obtained as a mixture of regioisomers, was prepared in a pure form from d-arabinose by a sequence of oximation/reduction/oxidation steps. Nucleophilic vinylation or allylation followed by ring-closing metathesis of the corresponding

  前所未有的支链吡咯并核苷和吲哚并核苷的合成是通过硝酮化学方法完成的。通过一系列的肟化/还原/氧化步骤，由d-阿拉伯糖以纯净的形式制备所需的酮硝酮，这是一种通常以区域异构体混合物形式获得的已知中间体。亲核性乙烯基化或烯丙基化，然后相应的N-allylpyrrolidines闭环易位，提供了靶向的亚氨基糖，这证明了水稻（GH31家族）α-葡萄糖苷酶的有效和选择性抑制剂。
• Total syntheses of hyacinthacine A2 and 7-deoxycasuarine by cycloaddition to a carbohydrate derived nitrone
  作者：Francesca Cardona、Enrico Faggi、Francesca Liguori、Martina Cacciarini、Andrea Goti

  DOI：10.1016/s0040-4039(03)00239-9

  日期：2003.3

  Practical syntheses of nitrone 8 by two different approaches from sugars are reported. Its use as a versatile intermediate in highly selective 1,3-dipolar cycloaddition reactions constitutes the key step for novel total syntheses of hyacinthacine A(2) (3) and 7-deoxycasuarine (20) by simple transformations of a common isoxazolidine adduct. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library
  作者：En-Lun Tsou、Sih-Yu Chen、Ming-Hsun Yang、Shih-Chi Wang、Ting-Ren Rachel Cheng、Wei-Chieh Cheng

  DOI：10.1016/j.bmc.2008.10.063

  日期：2008.12.15

  Inspired by polyhydroxylated pyrrolidine alkaloid natural products, a 18-membered library of 2-aryl polyhydroxylated pyrrolidines has been efficiently prepared in two or three synthetic steps from the known chiral cyclic nitrones with high yield and purity and excellent stereoselectivity. The inhibitory activity of all these compounds against various glycosidase enzymes was evaluated. Interestingly, 15 and 19 show better inhibitory activities than radicamine A ( 20) and B ( 18) against alpha-glucosidases. The IC50 values of 15 and 19 are 1.1 and 0.5 mu M, respectively. In this study, we also discovered the substituent(s) on the aryl ring could affect the inhibition potency and selectivity against glycosidases. (C) 2008 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.