(E)-(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxyhexanal O-benzyloxime | 112684-46-5

• 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: (E)-(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxyhexanal O-benzyloxime
• 英文别名: (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexanal O-benzyl oxime
• CAS: 112684-46-5
• 化学式: C₄₁H₄₃NO₆
• 分子量: 645.796
• InChiKey: YKGTWARLLNIJFK-WJCDOHCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.52
• 重原子数：
  48.0
• 可旋转键数：
  20.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  78.74
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (E)-(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxyhexanal O-benzyloxime 在 吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 7.5h， 生成 O-benzyl-N-[(1R,2S,3S,4R,5S)-2,3,4-tris-benzyloxy-5-benzyloxymethylcyclopentyl]-N-hydroxylamine
  参考文献：
  名称：

  Synthesis and Evaluation of Aminocyclopentitol Inhibitors of β-Glucosidases

  摘要：

  [GRAPHICS](1R,2S,3S,4R,5R)-4-Amino-5-(hydroxymethyl)cyclopentane-1,2,3-triol 1, prepared from D-glucose, inhibits beta-glucosidases from Caldocellum saccharolyticum (K-i = 1.8 x 10(-7) M) and from almonds (K-i = 3.4 x 10(-6) M). Inhibition is not influenced by N-ethylation (--> 15) but is strongly reduced upon N-acetylation (--> 12). Inversion of stereochemistry at C(5) (--> 14) has little effect on inhibition of beta-glucosidases. These experiments suggest that 1 acts as an analogue of a protonated beta-glucoside.

  DOI：

  10.1021/ol991252b
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 、 O-苄基羟胺 以 吡啶 、 甲醇 为溶剂， 反应 3.5h， 以84%的产率得到(E)-(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxyhexanal O-benzyloxime
  参考文献：
  名称：

  Synthesis and Evaluation of Aminocyclopentitol Inhibitors of β-Glucosidases

  摘要：

  [GRAPHICS](1R,2S,3S,4R,5R)-4-Amino-5-(hydroxymethyl)cyclopentane-1,2,3-triol 1, prepared from D-glucose, inhibits beta-glucosidases from Caldocellum saccharolyticum (K-i = 1.8 x 10(-7) M) and from almonds (K-i = 3.4 x 10(-6) M). Inhibition is not influenced by N-ethylation (--> 15) but is strongly reduced upon N-acetylation (--> 12). Inversion of stereochemistry at C(5) (--> 14) has little effect on inhibition of beta-glucosidases. These experiments suggest that 1 acts as an analogue of a protonated beta-glucoside.

  DOI：

  10.1021/ol991252b

文献信息

• Structure–activity relationships in aminocyclopentitol glycosidase inhibitors
  作者：Lucas Gartenmann Dickson、Emmanuel Leroy、Jean-Louis Reymond

  DOI：10.1039/b315704k

  日期：——

  substituents as aglycon mimics on the amine function were prepared and tested for inhibition of various glycosidases. N-benzyl-beta-D-gluco derivatives 1-4 and N-benzyl-beta-D-galacto derivative 5 inhibited beta-galactosidase and beta-glucosidase. N-benzyl-alpha-D-galacto aminocyclopentitol 6 strongly inhibited alpha-galactosidase. The inhibitory activities observed were generally stronger compared to those

  制备了具有β-D-葡萄糖，β-D-半乳糖和α-D-半乳糖的氨基取代的环戊糖类似物，所述烷基取代基作为糖胺苷元模拟胺功能，并测试了其对各种糖苷酶的抑制作用。N-苄基-β-D-葡萄糖衍生物1-4和N-苄基-β-D-半乳糖衍生物5抑制β-半乳糖苷酶和β-葡萄糖苷酶。N-苄基-α-D-半乳糖氨基环戊糖醇6强烈抑制α-半乳糖苷酶。与它们的伯胺类似物相比，观察到的抑制活性通常更强。进行了结构活性关系分析，包括来自35种不同的氨基环戊醇糖苷酶抑制剂的数据。据报道，任何一种酶的最强抑制作用都与氨基环戊糖醇和糖苷酶之间的立体化学完美匹配有关，
• Stereocontrolled Debenzylative Cycloetherification Reaction as a Route to Enantiopure <i>C</i>-Furanosides with Amino Substituents in the Side Chain
  作者：Karolina Tiara、Mykhaylo A. Potopnyk、Paweł Świder、Sławomir Jarosz

  DOI：10.1021/acs.joc.9b03247

  日期：2020.3.6

  A highly efficient methodology of the preparation of synthetically important tetrahydrofuran derivatives with an amino substituent in the side chain is reported. This process is based on the stereocontrolled debenzylative cycloetherification (DBCE) reaction applied for chirons from the d-gluco- and d-manno-series and provides derivatives with new stereogenic centers. The influence of the electron-withdrawing

  报道了制备在侧链中具有氨基取代基的重要的合成重要的四氢呋喃衍生物的高效方法。此过程基于立体控制的脱苄基环醚化（DBCE）反应，该反应适用于d-葡萄糖和d-甘露糖系列的Chiron，并为衍生物提供了新的立体生成中心。“在烧瓶中”和通过密度泛函理论（DFT）计算研究了存在于具有甲磺酰基离去基团的无环底物中的吸电子基团（EWG）对DBCE反应中反应性的影响。已证明具有苯并肟基（EWG = CHNOBn）的四氢呋喃衍生物非常适合用于随后的高度立体选择性格氏反应。