1,2-O-isopropylidene-3-C-(1'-hydroxyethyl)-5-N-benzyl-N-benzyloxycarbonyl-α-D-ribo-1,4-furanose | 1346677-52-8

• 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: 1,2-O-isopropylidene-3-C-(1'-hydroxyethyl)-5-N-benzyl-N-benzyloxycarbonyl-α-D-ribo-1,4-furanose
• CAS: 1346677-52-8
• 化学式: C₂₅H₃₁NO₇
• 分子量: 457.524
• InChiKey: ARRYIOANAVLDOY-WTEVXDJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  97.69
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3-C-(1'-hydroxyethyl)-5-N-benzyl-N-benzyloxycarbonyl-α-D-ribo-1,4-furanose 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis of anomeric 1,5-anhydrosugars as conformationally locked selective α-mannosidase inhibitors

  摘要：

  Anomeric 1,5-anhydrosugar 2 was synthesized from D-glucose derived N-Cbz protected aminodiol 8. The key step involves, acid catalyzed hydrolysis of 1,2-acetonide group in 8 to get hemiacetal that concomitantly undergoes formation of the pyranose ring by attack of C-3 hydroxyethyl group on anomeric C-1, leading to the formation of dioxabicyclo[3.2.1]octane skeleton which on hydrogenolyis gave 2. The glycosidase inhibitory activities of hydroxy-and amino-substituted anomeric 1,5-anhydrosugars 1 and 2, respectively, showed selective inhibition of alpha-mannosidase. These results were substantiated by molecular docking studies using WHAT IF software and AUTODOCK 4.0 program. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.046
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 sodium periodate 、 高氯酸 、 水 、 sodium cyanoborohydride 、 碳酸氢钠 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 11.0h， 生成 1,2-O-isopropylidene-3-C-(1'-hydroxyethyl)-5-N-benzyl-N-benzyloxycarbonyl-α-D-ribo-1,4-furanose
  参考文献：
  名称：

  Synthesis of anomeric 1,5-anhydrosugars as conformationally locked selective α-mannosidase inhibitors

  摘要：

  Anomeric 1,5-anhydrosugar 2 was synthesized from D-glucose derived N-Cbz protected aminodiol 8. The key step involves, acid catalyzed hydrolysis of 1,2-acetonide group in 8 to get hemiacetal that concomitantly undergoes formation of the pyranose ring by attack of C-3 hydroxyethyl group on anomeric C-1, leading to the formation of dioxabicyclo[3.2.1]octane skeleton which on hydrogenolyis gave 2. The glycosidase inhibitory activities of hydroxy-and amino-substituted anomeric 1,5-anhydrosugars 1 and 2, respectively, showed selective inhibition of alpha-mannosidase. These results were substantiated by molecular docking studies using WHAT IF software and AUTODOCK 4.0 program. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.046

文献信息

• γ-Hydroxyethyl piperidine iminosugar and N-alkylated derivatives: A study of their activity as glycosidase inhibitors and as immunosuppressive agents
  作者：Pramod R. Markad、Dhiraj P. Sonawane、Sougata Ghosh、Balu A. Chopade、Navnath Kumbhar、Thierry Louat、Jean Herman、Mark Waer、Piet Herdewijn、Dilip D. Dhavale

  DOI：10.1016/j.bmc.2014.09.034

  日期：2014.11

  An efficient and practical strategy for the synthesis of (3R, 4s, 5S)-4-(2-hydroxyethyl) piperidine-3,4,5-triol and its N-alkyl derivatives 8a-f, starting from the D-glucose, is reported. The chiral pool methodology involves preparation of the C-3-allyl-alpha-D-ribofuranodialdose 10, which was converted to the C-5-amino derivative 11 by reductive amination. The presence of C-3-allyl group gives an easy access to the requisite hydroxyethyl substituted compound 13. Intramolecular reductive aminocyclization of C-5 amino group with C-1 aldehyde provided the gamma-hydroxyethyl substituted piperidine iminosugar 8a that was N-alkylated to get N-alkyl derivatives 8b-f. Iminosugars 8a-f were screened against glycosidase enzymes. Amongst synthetic N-alkylated iminosugars, 8b and 8c were found to be a-galactosidase inhibitors while 8d and 8e were selective and moderate alpha-mannosidase inhibitors. In addition, immunomodulatory activity of compounds 8a-f was examined. These results were substantiated by molecular docking studies using AUTODOCK 4.2 programme. (C) 2014 Elsevier Ltd. All rights reserved.