(2S,3S,E)-2-((tert-butoxycarbonyl)amino)-1-hydroxyhex-4-en-3-yl benzoate | 1395097-47-8

• 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: (2S,3S,E)-2-((tert-butoxycarbonyl)amino)-1-hydroxyhex-4-en-3-yl benzoate
• CAS: 1395097-47-8
• 化学式: C₁₈H₂₅NO₅
• 分子量: 335.4
• InChiKey: IMUAUDIHLAIXQF-WSQYCBKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3-反-溴碳-2,2'-二甲基氧酸酯 在 吡啶 、 甲醇 、 copper(l) iodide 、 二甲基硫 、 对甲苯磺酸 、 红铝 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 9.0h， 生成 (2S,3S,E)-2-((tert-butoxycarbonyl)amino)-1-hydroxyhex-4-en-3-yl benzoate
  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

• Enantioselective Synthesis of Aminodiols by Sequential Rhodium‐Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine‐Based Catalysis
  作者：Joan Guasch、Irene Giménez‐Nueno、Ignacio Funes‐Ardoiz、Miguel Bernús、M. Isabel Matheu、Feliu Maseras、Sergio Castillón、Yolanda Díaz

  DOI：10.1002/chem.201705670

  日期：2018.3.26

  Regio‐ and stereoselective oxyamination of dienes through a tandem rhodium‐catalysed aziridination–nucleophilic opening affords racemic oxazolidinone derivatives, which undergo a kinetic resolution acylation process with amidine‐based catalysts (ABCs) to achieve s values of up to 117. This protocol was applied to the enantioselective synthesis of sphingosine.

  通过串联铑催化的叠氮化-亲核开口进行二烯的区域和立体选择性氧化胺化反应，得到外消旋的恶唑烷酮衍生物，其与with基催化剂（ABCs）进行动力学拆分酰化反应，可得到高达117的s值。采用了该协议对鞘氨醇的对映选择性合成。