(2S,3S)-methyl-1-(trityl)aziridine-2-carboxylic acid allyl ester | 1033066-83-9

• 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: (2S,3S)-methyl-1-(trityl)aziridine-2-carboxylic acid allyl ester
• 英文别名: (2R,3R)-allyl-3-methyl-1-1tritylaziridine-2-carboxylate
• CAS: 1033066-83-9
• 化学式: C₂₆H₂₅NO₂
• 分子量: 383.49
• InChiKey: PYLFFTFNHPLHFY-DEHGSCIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.31
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-methyl-1-(trityl)aziridine-2-carboxylic acid allyl ester 在 哌啶 、 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 27.58h， 生成
  参考文献：
  名称：

  New Charge-Bearing Amino Acid Residues That Promote β-Sheet Secondary Structure

  摘要：

  Proteinogenic amino acid residues that promote beta-sheet secondary structure are hydrophobic (e.g., Ile or Val) or only moderately polar (e.g., Thr). The design of peptides intended to display beta-sheet secondary structure in water typically requires one set of residues to ensure conformational stability and an orthogonal set, with charged side chains, to ensure aqueous solubility and discourage self-association. Here we describe new amino acids that manifest substantial beta-sheet propensity, by virtue of beta-branching, and also bear an ionizable group in the side chain.

  DOI：

  10.1021/ja510265e
• 作为产物：
  描述：

  L-threonine allyl ester 在 甲基磺酰氯 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成 (2S,3S)-methyl-1-(trityl)aziridine-2-carboxylic acid allyl ester
  参考文献：
  名称：

  New Charge-Bearing Amino Acid Residues That Promote β-Sheet Secondary Structure

  摘要：

  Proteinogenic amino acid residues that promote beta-sheet secondary structure are hydrophobic (e.g., Ile or Val) or only moderately polar (e.g., Thr). The design of peptides intended to display beta-sheet secondary structure in water typically requires one set of residues to ensure conformational stability and an orthogonal set, with charged side chains, to ensure aqueous solubility and discourage self-association. Here we describe new amino acids that manifest substantial beta-sheet propensity, by virtue of beta-branching, and also bear an ionizable group in the side chain.

  DOI：

  10.1021/ja510265e

文献信息

• Total Synthesis and Structure Assignment of Papuamide B, A Potent Marine Cyclodepsipeptide with Anti-HIV Properties
  作者：Weiqing Xie、Derong Ding、Weiwei Zi、Guangyu Li、Dawei Ma

  DOI：10.1002/anie.200705557

  日期：2008.3.31
• Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates
  作者：Keith O'Brien、Keith ó Proinsias、Fintan Kelleher

  DOI：10.1016/j.tet.2014.06.011

  日期：2014.8

  Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para-methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding beta-methyl azalanthionines have, so far, been unsuccessful. (C) 2014 Elsevier Ltd. All rights reserved.