5-benzyloxy-3-oxo-4S-(tritylamino)pentanoic acid allyl ester | 207509-00-0

• 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: 5-benzyloxy-3-oxo-4S-(tritylamino)pentanoic acid allyl ester
• 英文别名: prop-2-enyl (4S)-3-oxo-5-phenylmethoxy-4-(tritylamino)pentanoate
• CAS: 207509-00-0
• 化学式: C₃₄H₃₃NO₄
• 分子量: 519.64
• InChiKey: VFGUJNKXBMODAR-HKBQPEDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-benzyloxy-3-oxo-4S-(tritylamino)pentanoic acid allyl ester 在 吗啉 、 palladium diacetate 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 三甲基氯硅烷 、 cerium(III) chloride 、 sodium hexamethyldisilazane 、 sodium hydride 、 对苯醌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 41.5h， 生成 (E,2S,3S)-1-phenylmethoxy-2-(tritylamino)octadec-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 正丁基锂 、 三甲基氯硅烷 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 氯仿 、 乙腈 为溶剂， 反应 4.0h， 生成 5-benzyloxy-3-oxo-4S-(tritylamino)pentanoic acid allyl ester
  参考文献：
  名称：

  Highly Stereoselective Syntheses of syn- and anti-1,2-Amino Alcohols

  摘要：

  The reduction of N-protected amino ketones can be carried stereoselectively to produce either the syn- or anti-amino alcohol diastereomer. Carbamate-protected amino ketones can be reduced predictably and selectively to anti-amino alcohols with LiAlH(O-t-BU)(3) in ethanol at -78 degreesC. N-Trityl-protected amino ketones can be reduced selectively to syn-amino alcohols with LiAlH(O-t-Bu)(3) in THF at -5 degreesC.

  DOI：

  10.1021/jo010270f

文献信息

• A Stereocontrolled Synthesis of Monofluoro Ketomethylene Dipeptide Isosteres
  作者：Robert V. Hoffman、Junhua Tao

  DOI：10.1021/jo981334y

  日期：1999.1.1

  A simple, stereocontrolled synthesis of monofluoro ketomethylene dipeptide isosteres has been developed. N-Tritylated ketomethylene dipeptide isosteres, prepared from N-tritylated amino acids, are converted to their Z-TMS enol ethers and fluorinated with Selectfluor. There is cooperative stereocontrol between the N-tritylamine group and the alkyl group at C-2. The method is short (six steps), diastereoselective

  已经开发了简单的立体控制的单氟酮亚甲基二肽等排体的合成。由N-三苯甲基化的氨基酸制备的N-三苯甲基化的酮亚甲基二肽等位基因被转化为其Z-TMS烯醇醚并用Selectfluor进行氟化。N-三苯甲基胺基和C-2处的烷基之间存在协同立体控制。该方法很短（六个步骤），非对映选择性（85-> 95％）和对映选择性（> 95％）。
• 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.
• Highly Stereoselective Syntheses of <i>s</i><i>yn-</i> and <i>a</i><i>nti</i>-1,2-Amino Alcohols
  作者：Robert V. Hoffman、Najib Maslouh、Francisco Cervantes-Lee

  DOI：10.1021/jo010270f

  日期：2002.2.1

  The reduction of N-protected amino ketones can be carried stereoselectively to produce either the syn- or anti-amino alcohol diastereomer. Carbamate-protected amino ketones can be reduced predictably and selectively to anti-amino alcohols with LiAlH(O-t-BU)(3) in ethanol at -78 degreesC. N-Trityl-protected amino ketones can be reduced selectively to syn-amino alcohols with LiAlH(O-t-Bu)(3) in THF at -5 degreesC.