β-alanine trimethylsilyl ester | 5269-40-9

• 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: β-alanine trimethylsilyl ester
• 英文别名: β-Alanin-trimethylsilylester；beta-Alanine, TMS derivative；trimethylsilyl 3-aminopropanoate
• CAS: 5269-40-9
• 化学式: C₆H₁₅NO₂Si
• 分子量: 161.276
• InChiKey: LZYJRNYRJJQAEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  190.8±13.0 °C(Predicted)
• 密度：
  0.946±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  β-alanine trimethylsilyl ester 、 邻乙酰水杨酰氯 在 三乙胺 作用下， 生成 3-(2-acetoxybenzamido)propanoic acid
  参考文献：
  名称：

  Synthesis and Evaluation of Compounds That Facilitate the Gastrointestinal Absorption of Heparin

  摘要：

  A family of novel compounds (delivery agents) that promote the gastrointestinal absorption of USP heparin in rats and primates has been discovered. The delivery agents in combination with heparin were administered either orally or intracolonically in an aqueous propylene glycol solution and caused dramatic increases in both plasma heparin concentrations (anti-Factor Xa) and clotting times (APTT). Using one of the most effective delivery agents in this series, an estimated relative bioavailability of 8% can be achieved following oral administration to cynomolgus monkeys. To establish a correlation between the in vivo data and an in vitro parameter, immobilized artificial membrane (IAM) chromatography was performed. Log relative k' values were correlated to the efficiency of oral heparin delivery.

  DOI：

  10.1021/jm970811m
• 作为产物：
  描述：

  六甲基二硅氮烷 、 β-丙氨酸 以 甲苯 为溶剂， 生成 β-alanine trimethylsilyl ester
  参考文献：
  名称：

  Ruehlmann,K. et al., Journal fur praktische Chemie (Leipzig 1954), 1966, vol. 32, p. 37 - 42

  摘要：

  DOI：

文献信息

• A practical synthesis of free and protected guanidino acids from amino acids
  作者：Bansi Lal、A.K. Gangopadhyay

  DOI：10.1016/0040-4039(96)00299-7

  日期：1996.4

  Synthesis of protected guanidino acids in one pot reaction is achieved. Amino acids are treated with trimethylsilyl chloride, triethylamine, dicarbobenzoxy-S-methyl isothiourea in dichloromethane followed by removal of silyl group by treatment with methanol to give the corresponding carbobenzoxy guanidino acids.

  在一锅反应中合成了受保护的胍基酸。用二氯甲烷中的三甲基甲硅烷基氯，三乙胺，二碳苯甲氧基-S-甲基异硫脲处理氨基酸，然后通过用甲醇处理除去甲硅烷基，得到相应的碳苯甲酰胍基酸。
• On-Resin Carboxy Group Activation of ω-Amino Acids in Solid-Phase Synthesis­ of Philanthotoxin Analogues
  作者：Henrik Franzyk、Malene Jørgensen、Jerzy Jaroszewski、Matthias Witt

  DOI：10.1055/s-2005-872118

  日期：——

  A protocol for parallel solid-phase synthesis of ω-amino acid-elongated philanthotoxins was developed for exploration of structure-activity relationships for unnatural wasp toxin analogues. Several methods for on-resin activation of N-trityl-linked ω-amino acids were investigated, and the influence of chain length upon activation as pentafluorophenyl (Pfp) esters was examined. Comparison of Pfp-ester activation with phosphonium- and aminium/uronium-promoted coupling without pre-activation of the resin-bound carboxylic acids showed that only benzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate (PyBOP) exhibited a comparable efficiency. The present Pfp ester protocol gave high yields and purities of the resulting philanthotoxin analogues; however, in the case of γ-aminobutyric acid (GABA), use of PyBOP was required in order to avoid lactamization to 2-pyrrolidone.

  开发了α-氨基酸延长的花椒毒素的平行固相合成方案，用于探索非天然黄蜂毒素类似物的结构-活性关系。研究了几种 N-三苯甲基连接的 α-氨基酸的树脂上活化方法，并检查了链长对五氟苯基 (Pfp) 酯活化的影响。在未预活化树脂结合的羧酸的情况下，将 Pfp-酯活化与鏻和铵/脲促进的偶联进行比较表明，只有苯并三唑-1-基氧基三(吡咯烷)鏻六氟磷酸盐 (PyBOP) 表现出相当的效率。目前的 Pfp 酯方案得到了高产率和高纯度的花椒毒素类似物；然而，对于γ-氨基丁酸（GABA），需要使用PyBOP以避免内酰胺化为2-吡咯烷酮。
• Betulinic Acid Derivatives:  A New Class of Specific Inhibitors of Human Immunodeficiency Virus Type 1 Entry
  作者：Françoise Soler、Christèle Poujade、Michel Evers、Jean-Christophe Carry、Yvette Hénin、Anne Bousseau、Thierry Huet、Rudi Pauwels、Erik De Clercq、Jean-François Mayaux、Jean-Bernard Le Pecq、Norbert Dereu

  DOI：10.1021/jm950669u

  日期：1996.1.1

  A novel series of omega-aminoalkanoic acid derivatives of betulinic acid were synthesized and evaluated for their activity against human immunodeficiency virus (HIV). The anti-HIV-1 activity of several members of this new series was found to be in the nanomolar range in CEM 4 and MT-4 cell cultures. The optimization of the omega-aminoalkanoic acid side chain is described. The presence of an amide function within the side chain was found important for optimal activity. RPR 103611 (14g), a statine derivative, was found to be inactive against HIV-1 protease, reverse transcriptase, and integrase as well as on gp120/CD4 binding. ''Time of addition'' experiments suggested interaction with an early step of HIV-1 replication. As syncytium formation, but not virus-cell binding, seems to be affected, betulinic acid derivatives are assumed to interact with the postbinding virus-cell fusion process.
• Synthesis and Evaluation of Compounds That Facilitate the Gastrointestinal Absorption of Heparin
  作者：Andrea Leone-Bay、Duncan R. Paton、John Freeman、Christine Lercara、Doris O'Toole、David Gschneidner、Eric Wang、Elizabeth Harris、Connie Rosado、Theresa Rivera、Aldonna DeVincent、Monica Tai、Frank Mercogliano、Rajesh Agarwal、Harry Leipold、Robert A. Baughman

  DOI：10.1021/jm970811m

  日期：1998.3.1

  A family of novel compounds (delivery agents) that promote the gastrointestinal absorption of USP heparin in rats and primates has been discovered. The delivery agents in combination with heparin were administered either orally or intracolonically in an aqueous propylene glycol solution and caused dramatic increases in both plasma heparin concentrations (anti-Factor Xa) and clotting times (APTT). Using one of the most effective delivery agents in this series, an estimated relative bioavailability of 8% can be achieved following oral administration to cynomolgus monkeys. To establish a correlation between the in vivo data and an in vitro parameter, immobilized artificial membrane (IAM) chromatography was performed. Log relative k' values were correlated to the efficiency of oral heparin delivery.
• Ruehlmann,K. et al., Journal fur praktische Chemie (Leipzig 1954), 1966, vol. 32, p. 37 - 42
  作者：Ruehlmann,K. et al.

  DOI：——

  日期：——