methyl N-tritylleucinate | 18598-66-8

• 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: methyl N-tritylleucinate
• 英文别名: N-tritylleucine methyl ester；methyl N-trityl-(S)-leucinate；methyl (2S)-4-methyl-2-(tritylamino)pentanoate
• CAS: 18598-66-8
• 化学式: C₂₆H₂₉NO₂
• 分子量: 387.522
• InChiKey: NTSFIVRKEYVPIB-DEOSSOPVSA-N

物化性质

• 沸点：
  487.3±33.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl N-tritylleucinate 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 氯化亚砜 、 sodium hydride 、 碳酸氢钠 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 methyl (4S,trans)-4,5-dihydro-2-isobutyl-4-phenyl-5-carboxylate
  参考文献：
  名称：

  A practical diastereoselective synthesis of β-amino-α-hydroxy carboxylates

  摘要：

  Practical synthetic routes to beta-amino-alpha-hydroxy carboxylates (AHC) have been developed from amino acids. Reduction of beta-amino-alpha-keto esters 6 with NaBH4 was found to give anti-AHCs 7 in high de, which were efficiently converted to the corresponding syn-AHCs 8 via oxazolidine ring 10 formation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.009
• 作为产物：
  描述：

  L-亮氨酸 在 三乙胺 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 methyl N-tritylleucinate
  参考文献：
  名称：

  A practical diastereoselective synthesis of β-amino-α-hydroxy carboxylates

  摘要：

  Practical synthetic routes to beta-amino-alpha-hydroxy carboxylates (AHC) have been developed from amino acids. Reduction of beta-amino-alpha-keto esters 6 with NaBH4 was found to give anti-AHCs 7 in high de, which were efficiently converted to the corresponding syn-AHCs 8 via oxazolidine ring 10 formation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.009

文献信息

• Double Chirality Transmission in Trityl Amines: Sensing Molecular Dynamic Stereochemistry by Circular Dichroism and DFT Calculations
  作者：Jacek Ściebura、Jacek Gawroński

  DOI：10.1002/chem.201101699

  日期：2011.11.18

  than the methyl group (L). This is the case when a CD‐active trityl group at the nitrogen atom is used to report the chirality of the carbon substituent with two different sized groups (see scheme). The use of the trityl CD sensor allowed, in addition, the determination of the dominant absolute configuration of the nitrogen atom in chiral amines.

  配置：叔丁基在形式上可以比甲基（L）更“少”。当使用氮原子上的CD活性三苯甲基来报告带有两个不同大小的基团的碳取代基的手性时，就是这种情况（参见方案）。此外，使用三苯甲基CD传感器还可以确定手性胺中氮原子的主要绝对构型。
• Liquid detergents containing a peptide trifluoromethyl ketone
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0583535A1

  公开（公告）日：1994-02-23

  Aqueous liquid detergent compositions are described which comprise a proteolytic enzyme wherein the proteolytic activity is reversibly inhibited by a peptide trifluoromethyl ketone.

  所述的水基液体洗涤剂组合物包含一种蛋白水解酶，其中蛋白水解酶的活性被一种肽三氟甲基酮可逆地抑制。
• New inhibitors of renin that contain novel phosphostatine Leu-Val replacements
  作者：Joseph F. Dellaria、Robert G. Maki、Herman H. Stein、Jerome Cohen、David Whittern、Kennan Marsh、Daniel J. Hoffman、Jacob J. Plattner、Thomas J. Perun

  DOI：10.1021/jm00164a011

  日期：1990.2

  A novel series of renin inhibitors based on the Phe8-His9-Leu10-Val11 substructure of renin's natural substrate, angiotensinogen, is reported. These inhibitors retain the Phe8-His9 portion of the native substructure and employ novel phosphostatine Leu10-Val11 replacements (LVRs). The phosphostatine LVRs were prepared by condensing a dialkyl phosphonate ester stabilized anion with either N-t-Boc-amino aldehydes or N-tritylamino aldehydes (derived from the corresponding amino acid). Structure-activity relationships at the Leu10 side chain revealed that the LVR derived from L-cyclohexylalanine provided a 130-fold boost in potency over the LVR derived from L-leucine. The dialkyl ester moiety was varied and a loss in potency was incurred when the alkyl ester was chain extended or alpha-branched; dimethyl esters provided optimum potency. The phosphonate moiety was replaced by a half-acid half-ester phosphonate and dimethylphosphinate; both replacements lead to a loss in potency. The more potent inhibitors (IC50 = 20-50 nM) were found to be selective inhibitors for renin over porcine pepsin and bovine cathepsin D (little or no inhibition was observed at 10(-5) M).
• Improved stereocontrolled synthesis of threo peptidyl epoxides
  作者：Amnon Albeck、Rachel Persky

  DOI：10.1021/jo00082a026

  日期：1994.2
• LIQUID DETERGENTS CONTAINING PROTEOLYTIC ENZYME AND PROTEASE INHIBITORS
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0929640A1

  公开（公告）日：1999-07-21