(E,2S)-9-[tert-butyl(dimethyl)silyl]oxy-1-phenylmethoxy-2-(tritylamino)non-4-en-3-one | 207509-13-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (E,2S)-9-[tert-butyl(dimethyl)silyl]oxy-1-phenylmethoxy-2-(tritylamino)non-4-en-3-one
• CAS: 207509-13-5
• 化学式: C₄₁H₅₁NO₃Si
• 分子量: 633.946
• InChiKey: ZEXRQAHTVCUZJP-LLBAPVFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.47
• 重原子数：
  46
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E,2S)-9-[tert-butyl(dimethyl)silyl]oxy-1-phenylmethoxy-2-(tritylamino)non-4-en-3-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 、 (E,2S,3S)-9-[tert-butyl(dimethyl)silyl]oxy-1-phenylmethoxy-2-(tritylamino)non-4-en-3-ol
  参考文献：
  名称：

  A Synthesis of d-erythro- and l-threo-Sphingosine and Sphinganine Diastereomers via the Biomimetic Precursor 3-Ketosphinganine

  摘要：

  The four stereoisomers of sphingosine and sphinganine can be produced in protected form by a short, convergent, biomimetic synthesis from serine. Yields are good (26-38% overall from commercially available serine derivatives), and the stereoselectivities are excellent (>92% de, >95% eel. Several sphingosine L-threo-sphingosine analogues with modified, functionalized tails were prepared to demonstrate the versatility of the method.

  DOI：

  10.1021/jo980003i
• 作为产物：
  描述：

  O-苄基-L-丝氨酸 在 吗啉 、 甲醇 、 palladium diacetate 、 四(三苯基膦)钯 、 三甲基氯硅烷 、 sodium hexamethyldisilazane 、 sodium hydride 、 三乙胺 、 N,N'-羰基二咪唑 、 对苯醌 作用下， 以 四氢呋喃 为溶剂， 反应 38.0h， 生成 (E,2S)-9-[tert-butyl(dimethyl)silyl]oxy-1-phenylmethoxy-2-(tritylamino)non-4-en-3-one
  参考文献：
  名称：

  A Synthesis of d-erythro- and l-threo-Sphingosine and Sphinganine Diastereomers via the Biomimetic Precursor 3-Ketosphinganine

  摘要：

  The four stereoisomers of sphingosine and sphinganine can be produced in protected form by a short, convergent, biomimetic synthesis from serine. Yields are good (26-38% overall from commercially available serine derivatives), and the stereoselectivities are excellent (>92% de, >95% eel. Several sphingosine L-threo-sphingosine analogues with modified, functionalized tails were prepared to demonstrate the versatility of the method.

  DOI：

  10.1021/jo980003i

文献信息

• A Synthesis of <scp>d</scp>-<i>erythro</i>- and <scp>l</scp>-<i>threo</i>-Sphingosine and Sphinganine Diastereomers via the Biomimetic Precursor 3-Ketosphinganine
  作者：Robert V. Hoffman、Junhua Tao

  DOI：10.1021/jo980003i

  日期：1998.6.1

  The four stereoisomers of sphingosine and sphinganine can be produced in protected form by a short, convergent, biomimetic synthesis from serine. Yields are good (26-38% overall from commercially available serine derivatives), and the stereoselectivities are excellent (>92% de, >95% eel. Several sphingosine L-threo-sphingosine analogues with modified, functionalized tails were prepared to demonstrate the versatility of the method.