3-C-formylmethylene-1,2:5,6-di-O-isopropylidene-α-D-allo-furanose | 848415-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-C-formylmethylene-1,2:5,6-di-O-isopropylidene-α-D-allo-furanose
• 英文别名: 1,2;5,6-di-O-isopropylidene-3-C-(2'-oxoethyl)-α-D-allo-1,4-furanose；1,2:5,6-di-O-isopropylidene-3-C-(1'-acetaldehydo)-α-D-allo-1,4-furanose；2-[(3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-hydroxy-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-yl]acetaldehyde
• CAS: 848415-02-1
• 化学式: C₁₄H₂₂O₇
• 分子量: 302.324
• InChiKey: QSFFAGFASXDRRC-YNXVLUOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-C-formylmethylene-1,2:5,6-di-O-isopropylidene-α-D-allo-furanose 在 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到3-C-(2-hydroxyethyl)-1,2:5,6-di-O-isopropylidene-D-allofuranose
  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：

  1,2:5,6-二-o-异亚丙基-alpha-d-ribo-3-己呋喃核糖 在 lithium aluminium tetrahydride 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 3-C-formylmethylene-1,2:5,6-di-O-isopropylidene-α-D-allo-furanose
  参考文献：
  名称：

  糖部分连接的新异恶唑衍生物的合成

  摘要：

  这项工作报道了通过呋喃碘酸环的不同位置上的糖衍生物连接的异恶唑的合成，该过程是通过碘，碘化钾和碳酸氢钠对α，β-不饱和肟的分子内氧化环化作用而实现的。这些肟是从醛糖衍生物获得的。

  DOI：

  10.1002/jhet.5570410605

文献信息

• Synthesis of γ-Hydroxyalkyl Substituted Piperidine Iminosugars from <scp>d</scp>-Glucose
  作者：Rajendra S. Mane、K. S. Ajish Kumar、Dilip D. Dhavale

  DOI：10.1021/jo800044r

  日期：2008.4.1

  D-Glucose was converted to synthetic equivalent of meso-pentodialdose, namely 3-C-(1'-aminoethyl)-alpha-D-ribo-pento-dialdo-1,4-furanose 10 that gives an easy access to manipulate the aldehyde functionalities on either sides to get enantiomeric pair of 3. Thus, reduction of C5-aldehyde followed by hydrolysis of 1,2-acetonide functionality and reductive aminocyclization with C1-aldehyde afforded gamma-1,2-dihydroxyethyl piperidine iminosugar 3. On the other hand, first reductive aminocyclization with C5-aldehyde gave piperidine ring skeleton 12 that on removal of 1,2-acetonide and reduction of C1-aldehyde gave ent-3 while chopping of C1-aldehyde in 12 and reduction afforded gamma-hydroxymethyl piperidine immosugar 4.
• Synthesis of new isoxazoles derivatives attached to sugar moieties
  作者：Jorge M. Pinheiro、M. Isabel Ismael、J. Albertino Figueiredo、Artur M. S. Silva

  DOI：10.1002/jhet.5570410605

  日期：2004.11

  This work reports the synthesis of isoxazoles linked to sugar derivatives in different positions of furanosidic rings, by intramolecular oxidative cyclization of α,β-unsaturated oximes with iodine, potassium iodide and sodium hydrogen carbonate. These oximes were obtained from aldehyde-sugar derivatives.

  这项工作报道了通过呋喃碘酸环的不同位置上的糖衍生物连接的异恶唑的合成，该过程是通过碘，碘化钾和碳酸氢钠对α，β-不饱和肟的分子内氧化环化作用而实现的。这些肟是从醛糖衍生物获得的。
• Synthesis of anomeric 1,5-anhydrosugars as conformationally locked selective α-mannosidase inhibitors
  作者：Rajendra S. Mane、Sougata Ghosh、Shailza Singh、Balu A. Chopade、Dilip D. Dhavale

  DOI：10.1016/j.bmc.2011.09.046

  日期：2011.11

  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.