(2R,3R,4R,5S,6R)-4-(benzyloxy)-3-((tert-butoxycarbonyl)amino)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl acetate | 1395097-53-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5S,6R)-4-(benzyloxy)-3-((tert-butoxycarbonyl)amino)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl acetate
• CAS: 1395097-53-6
• 化学式: C₂₀H₂₉NO₇
• 分子量: 395.453
• InChiKey: KCZWCQFGRXGALH-SOGIYBJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  103.32
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S,6R)-4-(benzyloxy)-3-((tert-butoxycarbonyl)amino)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl acetate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以87%的产率得到(2R,3R,4R,6R)-4-(benzyloxy)-3-((tert-butoxycarbonyl)amino)-6-methyl-5-oxotetrahydro-2H-pyran-2-yl acetate
  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
• 作为产物：
  描述：

  (4S)-4-[(1S)-1-hydroxy-2-butynyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 吡啶 、 甲醇 、 四氧化锇 、 水 、 sodium hydride 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 红铝 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 、 甲苯 、 叔丁醇 为溶剂， 反应 15.0h， 生成 (2R,3R,4R,5S,6R)-4-(benzyloxy)-3-((tert-butoxycarbonyl)amino)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl acetate 、 4-(benzyloxy)-3-((tert-butoxycarbonyl)amino)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl acetate
  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