O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-oxyphthalimide | 390756-30-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-oxyphthalimide
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(1,3-dioxoisoindol-2-yl)oxyoxan-2-yl]methyl acetate
• CAS: 390756-30-6
• 化学式: C₂₂H₂₃NO₁₂
• 分子量: 493.424
• InChiKey: HZSCKBDHKVEXLR-MRSOFBGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-oxyphthalimide 在 PS-diethylenetriamine 、 溶剂黄146 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(E)-[(2R,3R)-2,4-dimethyl-3-phenylmethoxypentylidene]amino]oxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Convergent Synthesis of a Complex Oxime Library Using Chemical Domain Shuffling

  摘要：

  yThe synthesis of a complex hybrid oxime library is reported utilizing convergent ligation of alkoxyamine and carbonyl monomers via "chemical domain shuffling". Initial biological screening of the library against human small cell lung carcinoma (A549) cells led to the identification of a novel hybrid dimer in contrast to the corresponding monomeric compounds which were found to be inactive.

  DOI：

  10.1021/ol051023r
• 作为产物：
  描述：

  α-D(+)-五乙酰葡萄糖 在 氢溴酸 、 四丁基硫酸氢铵 、 sodium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 生成 O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-oxyphthalimide
  参考文献：
  名称：

  秋水仙碱的糖肽树状聚合物结合物对有丝分裂的抑制。

  摘要：

  已经制备了糖肽树状聚合物，其表面上带有四个或八个相同的糖苷部分（β-葡萄糖，α-半乳糖，α-N-乙酰基半乳糖或乳糖），分支内的天然氨基酸（Ser，Thr，His，Asp ，Glu，Leu，Val，Phe），2,3-二氨基丙酸作为分支单元，并在核心保留一个半胱氨酸残基。这些树状聚合物已被用作秋水仙碱的药物递送装置。秋水仙碱通过二硫键或硫醚键连接到半胱氨酸硫醇基团的树枝状聚合物上。在HeLa肿瘤细胞和未转化的小鼠胚胎成纤维细胞（MEF）中评估了糖肽树状聚合物结合物的生物学活性。发现通过干扰微管蛋白系统达到抑制细胞增殖所需的糖肽树状聚合物结合物的浓度比秋水仙碱浓度要高（IC50> 1 microM）。另一方面，糖肽树状大分子缀合物抑制HeLa细胞的增殖比MEF的增殖有效20到100倍。相比之下，非糖基化树状大分子和秋水仙碱本身对HeLa细胞的选择性是10倍或更低。

  DOI：

  10.1002/chem.200401294

文献信息

• Efficient preparation of carbohydrate–oligonucleotide conjugates (COCs) using oxime bond formation
  作者：Damien Forget、Olivier Renaudet、Eric Defrancq、Pascal Dumy

  DOI：10.1016/s0040-4039(01)01682-3

  日期：2001.10

  Chemoselective ligation of carbohydrates to oligonucleotides was accomplished by oxime bond formation. The conjugation was performed by reacting an oxyamino sugar with an oligonucleotide containing an aldehyde moiety at the 5'-end. The carbohydrate-oligonucleotide conjugates (COCs) were obtained in good yield without the need of a protection strategy and under mild aqueous conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Expedient synthesis of aminooxylated-carbohydrates for chemoselective access of glycoconjugates
  作者：Olivier Renaudet、Pascal Dumy

  DOI：10.1016/s0040-4039(01)01614-8

  日期：2001.10

  Herein, we describe an efficient preparation of various biologically important carbohydrate motifs bearing an aminooxy group at the anomeric position. These nucleophilic sugar analogues represent useful intermediates for the chemoselective preparation of glycoconjugates. The key glycosylation step involves the coupling of fluoro-activated protected sugar and N-hydroxyphthalimide in the presence of BF3. Et2O. Final deprotection and cleavage of the phthalimide moiety with methylhydrazine afforded new Glc-beta -ONH2 3, GalNAc-beta -ONH2 9, Glc-alpha -ONH2 14, Gal-alpha -ONH2 17 and Man-alpha -ONH2 20 derivatives with good yields. Compared to the literature results, the preparation of Gal-beta -ONH2 6, GalNAc-alpha -ONH2 11 and Lac-beta -ONH2 23 proved to be more efficient. (C) 2001 Elsevier Science Ltd. All rights reserved.