(S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester | 189459-10-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester
• 英文别名: Boc-Phe-Ser(TBDMS)-OMe；methyl (2S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]propanoate
• CAS: 189459-10-7
• 化学式: C₂₄H₄₀N₂O₆Si
• 分子量: 480.677
• InChiKey: VJIKZJXHZGMKNY-OALUTQOASA-N

物化性质

• 沸点：
  572.6±50.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester 在 劳森试剂 、 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 2-<(S)-1-t-butyloxycarbonylamino-2-phenyl-ethyl>-4-methoxycarbonyl-(R)-Δ2-thiazoline
  参考文献：
  名称：

  Synthesis of Peptidyl Aldehydes from Thiazolidines

  摘要：

  Peptidyl aldehydes were synthesized using thiazolidine peptides as precursors. Hydrolysis of the heterocycles is easily accomplished using cupper salts to furnish the peptidyl aldehydes with very good yield and with no epimerization. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00383-3
• 作为产物：
  描述：

  Boc-Phe-Ser-OMe 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到(S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester
  参考文献：
  名称：

  异戊烯化环肽躯干酰胺A（一种来自Lissoclinum sp。的细胞毒性代谢物）的全合成。

  摘要：

  描述了海洋来源的双烯丙基化环状肽躯干酰胺A及其C45差向异构体的全合成。

  DOI：

  10.1016/s0040-4039(01)00194-0

文献信息

• Synthesis of Highly Substituted Imidazolidine-2,4-dione (Hydantoin) through Tf₂O-Mediated Dual Activation of Boc-Protected Dipeptidyl Compounds
  作者：Hui Liu、Zhimin Yang、Zhengying Pan

  DOI：10.1021/ol502900j

  日期：2014.11.21

  Highly substituted chiral hydantoins were readily synthesized from simple dipeptides in a single step under mild conditions. This reaction proceeded through the dual activation of an amide and a tert-butyloxycarbonyl (Boc) protecting group by Tf2O-pyridine. This method was successfully applied in the preparation of a variety of biologically active compounds, including drug analogs and natural products

  高取代度的手性乙内酰脲很容易在温和的条件下一步一步由简单的二肽合成。该反应通过Tf 2 O-吡啶双重活化酰胺和叔丁氧羰基（Boc）保护基而进行。该方法已成功地用于制备多种生物活性化合物，包括药物类似物和天然产物。
• Total synthesis of the prenylated cyclopeptide trunkamide A, a cytotoxic metabolite from Lissoclinum sp.
  作者：Benedict McKeever、Gerald Pattenden

  DOI：10.1016/s0040-4039(01)00194-0

  日期：2001.3

  A total synthesis of the doubly prenylated cyclic peptide trunkamide A of marine origin, and also its C45 epimer, is described.

  描述了海洋来源的双烯丙基化环状肽躯干酰胺A及其C45差向异构体的全合成。
• Allyltrichlorostannane additions to chiral dipeptide aldehydes
  作者：Luiz C Dias、Edı́lson Ferreira

  DOI：10.1016/s0040-4039(01)01502-7

  日期：2001.10

  The first examples of successful allylsilane additions to chiral dipeptide aldehydes are described. Treatment of allylsilanes with tin tetrachloride at room temperature affords allyltrichlorostarnnane intermediates that reacts with dipeptide aldehydes to give 1,2-syn-homoallylic alcohols, potential intermediates for the synthesis of hydroxyethylene dipeptide isosteres. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Total synthesis of trunkamide A, a novel thiazoline-based prenylated cyclopeptide metabolite from Lissoclinum sp.
  作者：Benedict McKeever、Gerald Pattenden

  DOI：10.1016/s0040-4020(03)00294-1

  日期：2003.4

  Full details of a total synthesis of the doubly prenylated cyclic peptide trunkamide A of marine origin, and also its C45 epimer, are described.

  描述了海洋来源的双烯丙基化环状肽树干酰胺A及其C45差向异构体的全合成的全部细节。
• Synthesis of Peptidyl Aldehydes from Thiazolidines
  作者：Nathalie Galéotti*、Eric Plagnes、Patrick Jouin

  DOI：10.1016/s0040-4039(97)00383-3

  日期：1997.4

  Peptidyl aldehydes were synthesized using thiazolidine peptides as precursors. Hydrolysis of the heterocycles is easily accomplished using cupper salts to furnish the peptidyl aldehydes with very good yield and with no epimerization. (C) 1997 Published by Elsevier Science Ltd.