1-((2R,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenoxy-tetrahydro-pyran-2-ylmethyl)-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-urea | 884525-76-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((2R,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenoxy-tetrahydro-pyran-2-ylmethyl)-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-urea
• CAS: 884525-76-2
• 化学式: C₂₅H₃₉N₃O₁₅
• 分子量: 621.596
• InChiKey: KRUBVGOIEBRVQQ-YLHBMDLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.24
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  295.37
• 氢给体数：
  12.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6S,7S,7aR)-7-hydroxy-5-(hydroxymethyl)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,3a,5,6,7,7a-hexahydropyrano[2,3-d][1,3]oxazol-2-one 、 1-((2R,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenoxy-tetrahydro-pyran-2-ylmethyl)-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-urea 以 水 为溶剂， 反应 24.0h， 以87 mg的产率得到1-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-3-[[(2R,3S,4R,5R,6R)-5-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]carbamoylamino]-3,4-dihydroxy-6-phenoxyoxan-2-yl]methyl]urea
  参考文献：
  名称：

  Synthesis of Urea-Tethered Neoglycoconjugates and Pseudooligosaccharides in Water

  摘要：

  A novel approach to the synthesis of urea glycosides in aqueous media has been explored. Steyermark's glucopyranosyl oxazolidinone was found to be a good synthon for anchoring glucosyl moieties onto amines and thiols. The present method was successfully applied to establish a new route for the synthesis of urea-tethered neoglycoconjugates and pseudooligosaccharides in water.

  DOI：

  10.1021/ja056253f
• 作为产物：
  描述：

  (2R,3S,4R,5R,6R)-2-(acetoxymethyl)-6-phenoxy-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-3,4-diyl diacetate 在 palladium on activated charcoal 吡啶 、 甲醇 、 sodium azide 、 水 、 氢气 、 碳酸氢钠 、 溶剂黄146 、 三乙胺 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 79.5h， 生成 1-((2R,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenoxy-tetrahydro-pyran-2-ylmethyl)-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-urea
  参考文献：
  名称：

  Synthesis of Urea-Tethered Neoglycoconjugates and Pseudooligosaccharides in Water

  摘要：

  A novel approach to the synthesis of urea glycosides in aqueous media has been explored. Steyermark's glucopyranosyl oxazolidinone was found to be a good synthon for anchoring glucosyl moieties onto amines and thiols. The present method was successfully applied to establish a new route for the synthesis of urea-tethered neoglycoconjugates and pseudooligosaccharides in water.

  DOI：

  10.1021/ja056253f