(2R,3R,4R,5S,6R)-4-(benzoyloxy)-3-((tert-butoxycarbonyl)amino)-6-methyltetrahydro-2H-pyran-2,5-diyl diacetate | 1395097-52-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,4R,5S,6R)-4-(benzoyloxy)-3-((tert-butoxycarbonyl)amino)-6-methyltetrahydro-2H-pyran-2,5-diyl diacetate
• 英文别名: [(2R,3R,4R,5S,6R)-2,5-diacetyloxy-6-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]oxan-4-yl] benzoate
• CAS: 1395097-52-5
• 化学式: C₂₂H₂₉NO₉
• 分子量: 451.474
• InChiKey: WKPAGWSBHFMPAM-GUPBPSBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2S,3S,E)-2-((tert-butoxycarbonyl)amino)-1-hydroxyhex-4-en-3-yl benzoate 在 吡啶 、 四氧化锇 、 水 、 戴斯-马丁氧化剂 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 丙酮 、 叔丁醇 为溶剂， 生成 (2R,3R,4R,5S,6R)-4-(benzoyloxy)-3-((tert-butoxycarbonyl)amino)-6-methyltetrahydro-2H-pyran-2,5-diyl diacetate
  参考文献：
  名称：

  De Novo Synthesis of the Bacterial 2-Amino-2,6-Dideoxy Sugar Building Blocks d-Fucosamine, d-Bacillosamine, and d-Xylo-6-deoxy-4-ketohexosamine

  摘要：

  The cell-surface glycans on bacteria contain many monosaccharides that cannot be obtained by isolation from natural sources. Availability of differentially protected monosaccharides is therefore often limiting access to potential oligosaccharide vaccine antigens. D-Fucosamine, D-bacillosamine, and D-xylo-2,6-deoxy-4-ketohexosamine building blocks were prepared via a divergent de novo synthesis from L-Garner aldehyde. The route relies on a chelation-control assisted organometallic addition and an anti-selective dihydroxylation reaction.

  DOI：

  10.1021/ol3023227

文献信息

• <i>De novo</i> synthesis of D- and L-fucosamine containing disaccharides
  作者：Daniele Leonori、Peter H Seeberger

  DOI：10.3762/bjoc.9.38

  日期：——

  sources is currently limiting the access to the synthesis and the biological evaluation of complex bacterial cell-surface glycans. Here, we report the synthesis of D- and L-fucosamine building blocks by a de novo approach from L- and D-Garner aldehydes. These differentially protected monosaccharide building blocks were utilized to prepare disaccharides present on the surface of Pseudomonas aeruginosa

  无法从天然来源中分离的稀有单糖的可用性目前限制了复杂细菌细胞表面聚糖的合成和生物学评估。在这里，我们报告了通过 L- 和 D-Garner 醛的从头方法合成 D- 和 L- 岩藻糖胺构件。这些差异保护的单糖构建块用于制备存在于铜绿假单胞菌细菌表面的二糖。