(3aR,5R,6S,7S,7aR)-7-Hydroxy-5-hydroxymethyl-6-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[2,3-d]oxazol-2-one | 884525-66-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5R,6S,7S,7aR)-7-Hydroxy-5-hydroxymethyl-6-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[2,3-d]oxazol-2-one
• 英文别名: (3aR,5R,6S,7S,7aR)-7-hydroxy-5-(hydroxymethyl)-6-[(2S,3R,4S,5R,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
• CAS: 884525-66-0
• 化学式: C₁₃H₂₁NO₁₁
• 分子量: 367.31
• InChiKey: OAQBBQSGVLUIMT-GAXRGOLKSA-N

物化性质

• 熔点：
  230 °C (decomp)
• 沸点：
  828.4±65.0 °C(Predicted)
• 密度：
  1.77±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  187
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6S,7S,7aR)-7-Hydroxy-5-hydroxymethyl-6-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[2,3-d]oxazol-2-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 54.0h， 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
• 作为产物：
  描述：

  1-叠氮-1-脱氧-Β-D-吡喃乳糖苷 、 二氧化碳 在 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 以88%的产率得到(3aR,5R,6S,7S,7aR)-7-Hydroxy-5-hydroxymethyl-6-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[2,3-d]oxazol-2-one
  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

文献信息

• Synthesis of photoactivable oligosaccharide derivatives from 1,2-cyclic carbamate building blocks and study of their interaction with carbohydrate-binding proteins
  作者：Nikita M. Podvalnyy、Serge Chesnov、Paolo Nanni、Melanie Gut、Jason P. Holland、Thierry Hennet

  DOI：10.1016/j.carres.2021.108399

  日期：2021.10

  the low binding affinities of such interactions hamper the characterization of carbohydrate binding sites in the absence of three-dimensional structural models. To allow the identification of proteins interacting with specific carbohydrate epitopes, we have developed new photoactivable oligosaccharide probes. Oligosaccharides containing the 1,2-cyclic carbamate group were attached to building blocks

  尽管碳水化合物-蛋白质相互作用在生物学中广泛存在，但在缺乏三维结构模型的情况下，这种相互作用的低结合亲和力阻碍了碳水化合物结合位点的表征。为了识别与特定碳水化合物表位相互作用的蛋白质，我们开发了新的光活化寡糖探针。将含有 1,2-环氨基甲酸酯基团的寡糖连接到具有伯氨基的结构单元上，产生相应的脲衍生物。乳糖的环状氨基甲酸酯以及 3- 和 2'-岩藻糖基乳糖用于与含有光活化二氮丙啶、二苯甲酮或芳基叠氮基的结构单元缀合。测试所得寡糖衍生物与刺桐凝集素 (ECL)、橙木粉凝集素 (AAL) 和Ulex europaeus凝集素-I (UEA I) 的结合。我们发现含有芳基叠氮基光活化基团的配体成功连接到凝集素上。光活化反应保留了凝集素的完整性，因为没有看到蛋白质降解的迹象。质谱分析证实了一到三个寡糖探针之间的共价结合，这与所测试的凝集素的预期碳水化合物结合特性相匹配。因此，环状氨基甲酸酯衍生的寡糖
• Synthesis of Urea-Tethered Neoglycoconjugates and Pseudooligosaccharides in Water
  作者：Yoshiyasu Ichikawa、Yohei Matsukawa、Minoru Isobe

  DOI：10.1021/ja056253f

  日期：2006.3.1

  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.