O-benzyl-N-trityl-L-serine | 207509-19-1

• 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: O-benzyl-N-trityl-L-serine
• 英文别名: L-Trt-Ser(OBn)-OH；L-Tr-Ser(OBn)-OH；Tr-Ser(OBn)-OH；(2S)-3-phenylmethoxy-2-(tritylamino)propanoic acid
• CAS: 207509-19-1
• 化学式: C₂₉H₂₇NO₃
• 分子量: 437.538
• InChiKey: KZXXUIGNKMSOOX-MHZLTWQESA-N

物化性质

• 熔点：
  180-181 °C
• 沸点：
  589.7±50.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-benzyl-N-trityl-L-serine 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 、 N,N'-羰基二咪唑 、 对苯醌 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成
  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：

  三苯基氯甲烷 、 乙腈 在 三甲基氯硅烷 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 以82%的产率得到O-benzyl-N-trityl-L-serine
  参考文献：
  名称：

  N-trityl and N-phenylfluorenyl carboxyanhydrides of amino acids

  摘要：

  氨基酸经过衍生化处理，用于肽合成，通过转化为N-羧酸酐，然后通过三甲基苄基或苯基芴基团进行N-保护。

  公开号：

  US06093831A1

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％）。
• <i>N</i>-Trityl- and <i>N</i>-Phenylfluorenyl-<i>N</i>-carboxyanhydrides and Their Use in Dipeptide Synthesis
  作者：Tae Bo Sim、Henry Rapoport

  DOI：10.1021/jo981860p

  日期：1999.4.1
• Structural Characterization of an Enantiomerically Pure Amino Acid Imidazolide and Direct Formation of the β-Lactam Nucleus from an α-Amino Acid
  作者：Brian S. Gerstenberger、Jinzhen Lin、Yvette S. Mimieux、Lauren E. Brown、Allen G. Oliver、Joseph P. Konopelski

  DOI：10.1021/ol7025922

  日期：2008.2.1

  Decomposition of a diazo beta-ketoamide derived from N-trityl serine imidazolide and N-protected acetanilides provides, instead of the expected beta-acyloxindole product, an enantiomerically pure (EP) beta-lactam. The amino acid stereocenter is incorporated, the second chiral center is induced, and trityl protection of the beta-lactam ring is realized for the first time. The desired beta-acyloxindole is obtained from oxindole and Tr-Ser(OBn)-imidazole, the X-ray of which provides the first structural determination of an EP amino acid imidazolide.
• 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.
• Diazonamide Support Studies: Stereoselective Formation of the C10 Chiral Center in both the CDEFG and AEFG Fragments
  作者：Jinzhen Lin、Brian S. Gerstenberger、Nhu Y T. Stessman、Joseph P. Konopelski

  DOI：10.1021/ol8014336

  日期：2008.9.18

  The synthesis of both the AEFG macrolactam and the CDEFG bis-indole/tyrosine units found in the marine natural product diazonamide A is presented. Key to the success of the synthesis is the highly stereoselective direct C-arylation of an oxindole by an aryllead(IV) reagent derived from tyrosine.