6-azidohexyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranoside | 905440-32-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-azidohexyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranoside
• 英文别名: [(2S,3S,4R,5R,6R)-4,5-diacetyloxy-6-(6-azidohexoxy)-2-methyloxan-3-yl] acetate
• CAS: 905440-32-6
• 化学式: C₁₈H₂₉N₃O₈
• 分子量: 415.444
• InChiKey: NGTCLXIVWYQHPO-RNEPWOLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6-azidohexyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranoside 、 1-癸炔 在 copper diacetate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.17h， 以98%的产率得到6-(4-n-octyl-1H-1,2,3-triazol-1-yl)hexyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Sonochemistry:  A Powerful Way of Enhancing the Efficiency of Carbohydrate Synthesis

  摘要：

  [GRAPHICS]Using sonication as a means of facilitating organic reactions in carbohydrate chemistry was explored under the conditions used for traditional organic synthesis. An array of representative reactions, including hydroxy group manipulation ( acylation, protection/deprotection, acyl group migration), thioglycoside synthesis, azidoglycoside synthesis, 1,3-dipolar cycloaddition and reductive cleavage of benzylidene, commonly used in the synthesis of carbohydrate derivatives was examined. A series of glycosylation reactions that employ thioglycosides, glycosyl trichloroacetimidate, glycosyl bromide and glycosyl acetate as the glycosyl donors was also examined. Our results demonstrate that sonication can significantly shorten the reaction time, enhance the reactivity of reactant and lead to superior yield and excellent stereoselectivity. More importantly, a general protocol of glycosylation may finally be developed. Sonication is compatible to the conditions used for traditional organic synthesis. We believe that sonication can also be applied to other areas of synthetic processes.

  DOI：

  10.1021/jo060374w
• 作为产物：
  描述：

  1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.15h， 生成 6-azidohexyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Sonochemistry:  A Powerful Way of Enhancing the Efficiency of Carbohydrate Synthesis

  摘要：

  [GRAPHICS]Using sonication as a means of facilitating organic reactions in carbohydrate chemistry was explored under the conditions used for traditional organic synthesis. An array of representative reactions, including hydroxy group manipulation ( acylation, protection/deprotection, acyl group migration), thioglycoside synthesis, azidoglycoside synthesis, 1,3-dipolar cycloaddition and reductive cleavage of benzylidene, commonly used in the synthesis of carbohydrate derivatives was examined. A series of glycosylation reactions that employ thioglycosides, glycosyl trichloroacetimidate, glycosyl bromide and glycosyl acetate as the glycosyl donors was also examined. Our results demonstrate that sonication can significantly shorten the reaction time, enhance the reactivity of reactant and lead to superior yield and excellent stereoselectivity. More importantly, a general protocol of glycosylation may finally be developed. Sonication is compatible to the conditions used for traditional organic synthesis. We believe that sonication can also be applied to other areas of synthetic processes.

  DOI：

  10.1021/jo060374w

文献信息

• Combination of solid phase and solution phase synthesis of oligosaccharides using sonication
  作者：Christabel T. Tanifum、Jianjun Zhang、Cheng-Wei T. Chang

  DOI：10.1016/j.tetlet.2010.06.027

  日期：2010.8

  An approach that combines solid phase and solution phase synthesis of oligosaccharides via the assistance of sonication has been developed. By employing the traceless linker, the designed oligosaccharides can be obtained in pure form and, more importantly, ready for incorporation to aglycons of interest via ‘Click’ chemistry or amide linkage. The overall strategy will facilitate the studies of roles

  已经开发了通过超声处理结合寡糖的固相和溶液相合成的方法。通过使用无痕连接子，可以以纯净形式获得设计的寡糖，更重要的是，可以通过“点击”化学或酰胺键将寡糖掺入目标糖苷。总体策略将有助于研究碳水化合物在生物活性化合物中的作用。