3-tert-butoxycarbonylamino-2,2-bis(2,2,2-trifluoro-1,1-bis-trifluoromethylethoxymethyl)propionic acid

• 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: 3-tert-butoxycarbonylamino-2,2-bis(2,2,2-trifluoro-1,1-bis-trifluoromethylethoxymethyl)propionic acid
• 英文别名: 3-tert-butoxycarbonylamino-2,2-bis-(2,2,2-trifluoro-1,1-bis-trifluoromethyl-ethoxymethyl)-propionic acid；2,2-Bis[(nonafluoro-tert-butyloxy)methyl]-3-(Boc-amino)propionic acid；2,2-bis[[1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-yl]oxymethyl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• 化学式: C₁₈H₁₇F₁₈NO₆
• 分子量: 685.307
• InChiKey: CLEWMKNNQHDVCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  2-(4-methoxyphenyl)-5,5-bis(2,2,2-trifluoro-1,1-bis-trifluoromethylethoxymethyl)-[1,3]-dioxane 在 ruthenium trichloride 、 sodium periodate 、 三氯化铝 、 氯化亚砜 、 sodium azide 、 jones reagent 、 氢气 、 苯甲醚 、 三乙胺 作用下， 以 甲醇 、 四氯化碳 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 37.33h， 生成 3-tert-butoxycarbonylamino-2,2-bis(2,2,2-trifluoro-1,1-bis-trifluoromethylethoxymethyl)propionic acid
  参考文献：
  名称：

  The Synthesis of a Geminally Perfluoro-tert-butylated β-Amino Acid and its Protected Forms as a Potential Pharmacokinetic Modulator and Reporter for Peptide-Based Pharmaceuticals

  摘要：

  To modulate and report the pharmacokinetics of peptide-based pharmaceuticals, a novel geminally perfluoro-tert-butylated beta-amino acid (beta Fa) and its Fmoc- and Boc-protected forms were designed and synthesized. beta Fa was incorporated into a model tripeptide via standard solid-phase chemistry. Both the amino acid (free and protected) and the tripeptide show a sharp singlet F-19 NMR signal. Reversed-phase chromatography and 1-octanol/water partition measurements demonstrate that beta Fa is extremely hydrophobic.

  DOI：

  10.1021/jo0616308

文献信息

• WO2008/34093
  申请人：——

  公开号：——

  公开（公告）日：——
• HIGHLY FLUORINATED BETA-AMINO ACIDS AND METHODS OF MAKING AND USING SAME
  申请人：Yu Bruce

  公开号：US20090259020A1

  公开（公告）日：2009-10-15

  Disclosed are compounds having the structure: wherein R 1a and R 1b are independently H, alkyl, F, or fluoroalkyl; wherein R 2a , R 2b , R 2a′ , and R 2b′ are independently H, alkyl, F, fluoroalkyl, aryl, or alkenyl; wherein R 3 is OH, alkoxyl, NH 2 , alkylamino, or dialkylamino; wherein R 4a and R 4b are independently H, alkyl, acyl, or alkyloxycarbonyl; wherein R 11 , R 12 , R 13 , R 21 , R 22 , and R 23 are independently H, alkyl, F, or fluoroalkyl; and wherein C0, C1, C2, and C2′ are independently chiral or achiral. Also disclosed are processes for making a fluorinated β-amino acid comprising the steps of: providing a diol; treating the diol with a thionyl halide with oxidative workup; reacting the product with an azide salt to yield an azido group; oxidizing the product to yield a carboxyl group; and reducing the azido group to yield an amino group. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
• US8052961B2
  申请人：——

  公开号：US8052961B2

  公开（公告）日：2011-11-08
• The Synthesis of a Geminally Perfluoro-<i>tert</i>-butylated β-Amino Acid and its Protected Forms as a Potential Pharmacokinetic Modulator and Reporter for Peptide-Based Pharmaceuticals
  作者：Zhong-Xing Jiang、Y. Bruce Yu

  DOI：10.1021/jo0616308

  日期：2007.2.1

  To modulate and report the pharmacokinetics of peptide-based pharmaceuticals, a novel geminally perfluoro-tert-butylated beta-amino acid (beta Fa) and its Fmoc- and Boc-protected forms were designed and synthesized. beta Fa was incorporated into a model tripeptide via standard solid-phase chemistry. Both the amino acid (free and protected) and the tripeptide show a sharp singlet F-19 NMR signal. Reversed-phase chromatography and 1-octanol/water partition measurements demonstrate that beta Fa is extremely hydrophobic.