3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl iodide | 128878-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl iodide
• 英文别名: 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-glucopyranosyl iodide；[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-azido-6-iodooxan-2-yl]methyl acetate
• CAS: 128878-99-9
• 化学式: C₁₂H₁₆IN₃O₇
• 分子量: 441.179
• InChiKey: JUWPYVJKIMHAEP-OOCWMUITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl iodide 生成 [(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-azido-6-cyanooxan-2-yl]methyl acetate
  参考文献：
  名称：

  BEMILLER, JAMES N.;BLAZIS, VINCENT J.;MYERS, ROBERT W., J. CARBOHYDR. CHEM., 9,(1990) N, C. 39-57

  摘要：

  DOI：
• 作为产物：
  描述：

  2-叠氮基-2-脱氧-D-吡喃葡萄糖1,3,4,6-四乙酸酯 在 碘 、 氢化铝 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl iodide
  参考文献：
  名称：

  [EN] GLYCOSYLATED ANTITUMOR ETHER LIPIDS AS NOVEL CANCER STEM CELL CYTOTOXIC AGENTS
  [FR] ÉTHER-LIPIDES ANTICANCÉREUX GLYCOSYLÉS EN TANT QUE NOUVEAUX AGENTS CYTOTOXIQUES DE CELLULES SOUCHES CANCÉREUSES

  摘要：

  糖基化抗肿瘤醚脂质（GAELs）是有效的细胞毒性剂，可针对癌干细胞。此外，将通过一种与半胱氨酸蛋白酶无关的途径杀死细胞的GAELs与通过凋亡杀死细胞的药物结合，将导致消除分化的肿瘤细胞和未分化的癌干细胞，从而消除肿瘤并预防复发。

  公开号：

  WO2013116949A1

文献信息

• Glycosyl selenoacetates: versatile building blocks for the preparation of stereoselective selenoglycosides and selenium linked disaccharides
  作者：Tapasi Manna、Anup Kumar Misra

  DOI：10.1039/c9ob01623f

  日期：——

  Glycosyl selenoacetate derivatives were prepared by the treatment of glycosyl halide with potassium selenocyanate followed by acetylation of in situ generated glycosyl selenols in one pot. A variety of selenoglycosides and selenium linked disaccharide derivatives were prepared in very good to excellent yields using glycosyl selenoacetates as stable building blocks under mild reaction conditions.

  通过用硒氰酸钾处理糖基卤化物，然后在一锅中将原位产生的糖基硒醇乙酰化，来制备糖基硒酸乙酸酯衍生物。在温和的反应条件下，使用硒基硒酸乙酸酯作为稳定的结构单元，可以很好地制备出多种硒代糖苷和硒键联的二糖衍生物。
• GLYCOSYLATED ANTITUMOR ETHER LIPIDS AS NOVEL CANCER STEM CELL CYTOTOXIC AGENTS
  申请人：UNIVERSITY OF MANITOBA

  公开号：US20150011486A1

  公开（公告）日：2015-01-08

  Glycosylated antitumor ether lipids (GAELs) are effective cytotoxic agents against cancer stem cells. Furthermore, combining GAELs which kill cells by a caspase-independent pathway with agents that kill cells by apoptosis will lead to elimination of the differentiated tumor cells and the undifferentiated cancer stem cells leading to an elimination of the tumor and preventing recurrence.

  糖基化抗肿瘤醚类脂质（GAELs）是有效的细胞毒性剂，可针对癌症干细胞。此外，将能够通过非半胱氨酸依赖途径杀死细胞的GAELs与能够通过凋亡杀死细胞的药物结合使用，将导致消除分化的肿瘤细胞和未分化的癌症干细胞，从而消除肿瘤并防止复发。
• Glycosylated antitumor ether lipids as novel cancer stem cell cytotoxic agents
  申请人：UNIVERSITY OF MANITOBA

  公开号：US11261210B2

  公开（公告）日：2022-03-01

  Glycosylated antitumor ether lipids (GAELs) are effective cytotoxic agents against cancer stem cells. Furthermore, combining GAELs which kill cells by a caspase-independent pathway with agents that kill cells by apoptosis will lead to elimination of the differentiated tumor cells and the undifferentiated cancer stem cells leading to an elimination of the tumor and preventing recurrence.

  糖基化抗肿瘤醚脂（GAELs）是针对癌症干细胞的有效细胞毒剂。此外，糖基化抗肿瘤醚脂与通过细胞凋亡杀死细胞的药剂结合使用，可通过不依赖卡巴酶的途径杀死细胞，从而消除已分化的肿瘤细胞和未分化的癌症干细胞，从而消除肿瘤并防止复发。
• Iodine Promoted Glycosylation with Glycosyl Iodides: α‐Glycoside Synthesis
  作者：Renate van Well、K. Ravindranathan Kartha、Robert Field

  DOI：10.1081/car-200067028

  日期：2005.8.1

  Glycosidation of fully acetylated glucopyranosyl iodide with methanol under the influence of iodine gave a-glucoside selectively. Use of less reactive acceptors led to the formation of alpha/beta-mixtures. Glycosylations with fully benzoylated glucosyl iodide yielded beta-glucosides only. In contrast, iodine-promoted glycosylation of serine and threonine with 2-azido-2-deoxy-glycosyl iodides, easily obtained in three steps, proceeded smoothly, resulting in only alpha-linked products in high yield in most cases.