3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranose | 215314-53-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranose
• CAS: 215314-53-7
• 化学式: C₂₀H₁₇Cl₄NO₁₀
• 分子量: 573.168
• InChiKey: YUEXIQFQLRXFAO-JAOOAAHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  145.74
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranose 在 咪唑 、 sodium methylate 、 四丁基碘化铵 、 三丁基氧化锡 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 2-{(2S,4R,5S,6R)-6-Benzyloxymethyl-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-4,5,6,7-tetrachloro-isoindole-1,3-dione
  参考文献：
  名称：

  Lay, Luigi; Manzoni, Leonardo; Schmidt, Richard R., Carbohydrate Research, 1998, vol. 310, # 3, p. 159 - 172

  摘要：

  DOI：
• 作为产物：
  描述：

  1-phenylsulfenyl-3,4,6-tri-O-acetyl-1,2-dideoxy-2-N-tetrachlorophthalimido-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 丙酮 为溶剂， 反应 0.25h， 生成 3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranose
  参考文献：
  名称：

  Lay, Luigi; Manzoni, Leonardo; Schmidt, Richard R., Carbohydrate Research, 1998, vol. 310, # 3, p. 159 - 172

  摘要：

  DOI：

文献信息

• <i>N</i>-Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity
  作者：Agata Walczewska、Daria Grzywacz、Dorota Bednarczyk、Małgorzata Dawgul、Andrzej Nowacki、Wojciech Kamysz、Beata Liberek、Henryk Myszka

  DOI：10.3762/bjoc.11.97

  日期：——

  Diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside is a synthetic saponin exhibiting attractive pharmacological properties. Different pathways tested by us to obtain this glycoside are summarized here. Moreover, the synthesis of N-alkyl and N,N-dialkyl derivatives of the glucopyranoside is presented. Evaluation of antibacterial and antifungal activities of these derivatives indicates that they have no inhibitory activity against Gram-negative bacteria, whereas many of the tested N-alkyl saponins were found to inhibit the growth of Gram-positive bacteria and human pathogenic fungi.

  Diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside是一种具有吸引人的药理特性的合成皂苷。我们测试了不同的途径来获得这种糖苷，这里总结了这些途径。此外，还介绍了合成葡萄糖吡喃糖苷的N-烷基和N,N-二烷基衍生物。对这些衍生物的抗菌和抗真菌活性评估表明，它们对革兰氏阴性菌没有抑制活性，而许多经过测试的N-烷基皂苷被发现抑制了革兰氏阳性菌和人类病原真菌的生长。
• Glucosamine derived DISAL donors for stereoselective glycosylations under neutral conditions
  作者：Susanne Grathe、Mikkel B. Thygesen、Kim Larsen、Lars Petersen、Knud J. Jensen

  DOI：10.1016/j.tetasy.2005.02.029

  日期：2005.4

  DISAL (methyl 3,5-dinitrosa/icylate) D-glcosyl, D-galactosyl, D-mannosyl, and L-quinovosyl donors have previously provided the efficient glycosylation of a range of substrates under either strictly neutral, mildly basic, or very mildly Lewis acidic (LiClO4) conditions. Herein we report the synthesis of new glucosamine DISAL donors, carrying N-TCP, -Troc, or -TFAc protecting groups, and their use in beta-(1,2-trans) selective glycosylations, primarily in NMP in the absence of any added Lewis acids, or in CH3NO2 with LiClO4. Finally, precise microwave heating proved effective in promoting the difficult glycosylation of the 3-OH of a glucosamine derivative. (c) 2005 Elsevier Ltd. All rights reserved.