(S)-2-Amino-N-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(3-hydroxy-phenyl)-ethyl]-propionamide | 167423-70-3

• 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: (S)-2-Amino-N-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(3-hydroxy-phenyl)-ethyl]-propionamide
• CAS: 167423-70-3
• 化学式: C₁₇H₃₀N₂O₃Si
• 分子量: 338.522
• InChiKey: OXXVJWAFIHBXHN-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  84.58
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-N-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(3-hydroxy-phenyl)-ethyl]-propionamide 在 盐酸 、 二苯基磷酸 、 水 、 三乙胺 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 19.0h， 生成 (R)-4-Methyl-2-methylamino-pentanoic acid ((8R,11S,14R)-8-hydroxymethyl-11-methyl-18-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaen-14-yl)-amide
  参考文献：
  名称：

  Synthesis of Modified Carboxyl Binding Pockets of Vancomycin and Teicoplanin

  摘要：

  Sixteen-membered macrocycle 3 and 16+14 bicyclic compound 4, incorporating a terminal primary hydroxyl group in the peptide sequence, have been designed and synthesized. The syntheses feature the use of an efficient cycloetherification based on an intramolecular SNAr reaction for the formation of biaryl ether bonds. Cyclization of linear tetrapeptide 30, prepared via a convergent [2+2] segment coupling between 26 and 29, gave macrocycle 31 (P configuration) as a single isolable atropisomer. Removal of the Boc protecting group afforded the modified carboxyl binding pocket of vancomycin 3. A sequential 2-fold intramolecular SNAr reaction has been used to construct the model bicyclic system (i.e. 4) of the D-O-E-F-O-G ring of teicoplanin. Cyclization conditions (CsF, DMF, room temperature) are sufficiently mild that the configuration of the racemization-prone arylglycine residue was not affected. Chiral building blocks such as D-(1R)-[2-[(tert-butyldimethylsilyl)oxy] 1-[3-(allyloxy)phenyl]ethyl]amine 16, and L-(S)-N-Boc-[3-(isopropyloxy)phenyl]glycine (32) were synthesized employing Evans' asymmetric azidation method, while L-(S)-4-fluoro-3-nitrophenylalanine methyl ester 23 was prepared using Schollkopf's bislactim ether as chiral glycine template. Compound 3 showed interesting conformational properties compared to vancomycin and its binding with Ac-D-Ala was studied by NMR titration experiments. A dissociation constant (K-d = 5 x 10(-4)) was calculated by a curve fitting method. Compound 4 is currently the most advanced synthetic intermediate toward the total synthesis of teicoplanin.

  DOI：

  10.1021/jo961412m
• 作为产物：
  描述：

  {(S)-1-[(R)-1-(3-Allyloxy-phenyl)-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-ethyl}-carbamic acid allyl ester 在 锂硼氢 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (S)-2-Amino-N-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(3-hydroxy-phenyl)-ethyl]-propionamide
  参考文献：
  名称：

  Synthesis of Modified Carboxyl Binding Pockets of Vancomycin and Teicoplanin

  摘要：

  Sixteen-membered macrocycle 3 and 16+14 bicyclic compound 4, incorporating a terminal primary hydroxyl group in the peptide sequence, have been designed and synthesized. The syntheses feature the use of an efficient cycloetherification based on an intramolecular SNAr reaction for the formation of biaryl ether bonds. Cyclization of linear tetrapeptide 30, prepared via a convergent [2+2] segment coupling between 26 and 29, gave macrocycle 31 (P configuration) as a single isolable atropisomer. Removal of the Boc protecting group afforded the modified carboxyl binding pocket of vancomycin 3. A sequential 2-fold intramolecular SNAr reaction has been used to construct the model bicyclic system (i.e. 4) of the D-O-E-F-O-G ring of teicoplanin. Cyclization conditions (CsF, DMF, room temperature) are sufficiently mild that the configuration of the racemization-prone arylglycine residue was not affected. Chiral building blocks such as D-(1R)-[2-[(tert-butyldimethylsilyl)oxy] 1-[3-(allyloxy)phenyl]ethyl]amine 16, and L-(S)-N-Boc-[3-(isopropyloxy)phenyl]glycine (32) were synthesized employing Evans' asymmetric azidation method, while L-(S)-4-fluoro-3-nitrophenylalanine methyl ester 23 was prepared using Schollkopf's bislactim ether as chiral glycine template. Compound 3 showed interesting conformational properties compared to vancomycin and its binding with Ac-D-Ala was studied by NMR titration experiments. A dissociation constant (K-d = 5 x 10(-4)) was calculated by a curve fitting method. Compound 4 is currently the most advanced synthetic intermediate toward the total synthesis of teicoplanin.

  DOI：

  10.1021/jo961412m

文献信息

• Palladium catalyzed reductive deprotection of Alloc: Transprotection and peptide bond formation
  作者：René Beugelmans、Luc Neuville、Michèle Bois-Choussy、Jacqueline Chastanet、Jieping Zhu

  DOI：10.1016/0040-4039(95)00449-m

  日期：1995.5

  N-allyloxycarbonyl group could be efficiently removed using sodium borohyride as hydride donnor in the presence of catalytic amount of palladium (0). The conditions were applied to chemoselective protecting group transformation (transprotection) and peptide bond formation.