(R)-2-azido-3-[(dimethyl)phenylsilyl]propionic acid | 297165-65-2

• 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: (R)-2-azido-3-[(dimethyl)phenylsilyl]propionic acid
• 英文别名: L-β-(Dimethylphenylsilyl)alanine；L-[(dimethyl)phenylsilyl]alanine；(r)-2-Amino-3-[dimethyl(phenyl)silyl]-propionic acid；(2R)-2-amino-3-[dimethyl(phenyl)silyl]propanoic acid
• CAS: 297165-65-2
• 化学式: C₁₁H₁₇NO₂Si
• 分子量: 223.347
• InChiKey: NUJKJRUPWGDRHG-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  potassium cyanate 、 (R)-2-azido-3-[(dimethyl)phenylsilyl]propionic acid 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 3.0h， 以84%的产率得到L-2-carbamoylamino-3-[(dimethyl)phenylsilyl]propionic acid
  参考文献：
  名称：

  Enzymatic synthesis of enantiomerically enriched d- and l-3-silylated alanines by deracemization of dl-5-silylmethylated hydantoins

  摘要：

  The hydantoinase process was shown to be extendable to the production of highly lipophilic, silicon-containing amino acids. Two hydantoinases of different origin and stereoselectivities and one L-N-carbamoylase were used for the highly stereoselective bioconversion of (dimethyl)phenylsilyl- and 1-methyl-1-silacyclopentyl substituted alanine derivatives. The enantiomeric purities and absolute configuration of the products were determined with reference compounds that were synthesized with the aid of the Evans oxazolidinone auxiliary. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00028-3
• 作为产物：
  描述：

  3-[(dimethyl)phenylsilyl]propionic acid 在 platinum(IV) oxide lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 N,N,N',N'-tetramethylguanidinium azide 、 氢气 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 19.5h， 生成 (R)-2-azido-3-[(dimethyl)phenylsilyl]propionic acid
  参考文献：
  名称：

  Enzymatic synthesis of enantiomerically enriched d- and l-3-silylated alanines by deracemization of dl-5-silylmethylated hydantoins

  摘要：

  The hydantoinase process was shown to be extendable to the production of highly lipophilic, silicon-containing amino acids. Two hydantoinases of different origin and stereoselectivities and one L-N-carbamoylase were used for the highly stereoselective bioconversion of (dimethyl)phenylsilyl- and 1-methyl-1-silacyclopentyl substituted alanine derivatives. The enantiomeric purities and absolute configuration of the products were determined with reference compounds that were synthesized with the aid of the Evans oxazolidinone auxiliary. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00028-3

文献信息

• Silicon-Containing Amino Acids and Peptides. Asymmetric Synthesis of (Trialkylsilyl)alanines
  作者：Robert D. Walkup、Derek C. Cole、Bruce R. Whittlesey

  DOI：10.1021/jo00113a053

  日期：1995.4
• Enzymatic synthesis of enantiomerically enriched d- and l-3-silylated alanines by deracemization of dl-5-silylmethylated hydantoins
  作者：Richard J. Smith、Markus Pietzsch、Thomas Waniek、Christoph Syldatk、Stefan Bienz

  DOI：10.1016/s0957-4166(01)00028-3

  日期：2001.2

  The hydantoinase process was shown to be extendable to the production of highly lipophilic, silicon-containing amino acids. Two hydantoinases of different origin and stereoselectivities and one L-N-carbamoylase were used for the highly stereoselective bioconversion of (dimethyl)phenylsilyl- and 1-methyl-1-silacyclopentyl substituted alanine derivatives. The enantiomeric purities and absolute configuration of the products were determined with reference compounds that were synthesized with the aid of the Evans oxazolidinone auxiliary. (C) 2001 Elsevier Science Ltd. All rights reserved.