(R)-N-benzyloxycarbonyl tyrosinamide | 226699-26-9

• 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: (R)-N-benzyloxycarbonyl tyrosinamide
• 英文别名: benzyl N-[(1R)-1-carbamoyl-2-(4-hydroxyphenyl)ethyl]carbamate；benzyl N-[(2R)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamate
• CAS: 226699-26-9
• 化学式: C₁₇H₁₈N₂O₄
• 分子量: 314.341
• InChiKey: DJPCVJYIWLEUBO-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-N-benzyloxycarbonyl tyrosinamide 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以87%的产率得到[(R)-1-Carbamoyl-2-(4-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  A stereocontrolled synthesis of a new class of 3,4,5,6-tetrahydropyrimidine-based chiral amino acids

  摘要：

  The stereocontrolled synthesis of seven 2-substituted-4-carboxy-3,4,5,6-tetrahydropyrimidines bearing either one chiral center at C-4 or two chiral centers at C-4 and C-8 was performed by condensation of (S)- or (R)-2, 4-diaminobutyric acid (Daba) with iminoethers derived from glycine. (S)- and (R serine, (S)- and (R)-tyrosine. Under the conditions reported, epimerization was always completely prevented at the C-4 center, whereas at the C-8 center, it was completely avoided in the case of tyrosine derivatives and considerably diminished for the serine derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00177-5
• 作为产物：
  描述：

  N-苄氧羰基-D-酪氨酸 在 氨 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.08h， 生成 (R)-N-benzyloxycarbonyl tyrosinamide
  参考文献：
  名称：

  A stereocontrolled synthesis of a new class of 3,4,5,6-tetrahydropyrimidine-based chiral amino acids

  摘要：

  The stereocontrolled synthesis of seven 2-substituted-4-carboxy-3,4,5,6-tetrahydropyrimidines bearing either one chiral center at C-4 or two chiral centers at C-4 and C-8 was performed by condensation of (S)- or (R)-2, 4-diaminobutyric acid (Daba) with iminoethers derived from glycine. (S)- and (R serine, (S)- and (R)-tyrosine. Under the conditions reported, epimerization was always completely prevented at the C-4 center, whereas at the C-8 center, it was completely avoided in the case of tyrosine derivatives and considerably diminished for the serine derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00177-5

文献信息

• A stereocontrolled synthesis of a new class of 3,4,5,6-tetrahydropyrimidine-based chiral amino acids
  作者：Adel Zamri、Finton Sirockin、Mohamed A. Abdallah

  DOI：10.1016/s0040-4020(99)00177-5

  日期：1999.4

  The stereocontrolled synthesis of seven 2-substituted-4-carboxy-3,4,5,6-tetrahydropyrimidines bearing either one chiral center at C-4 or two chiral centers at C-4 and C-8 was performed by condensation of (S)- or (R)-2, 4-diaminobutyric acid (Daba) with iminoethers derived from glycine. (S)- and (R serine, (S)- and (R)-tyrosine. Under the conditions reported, epimerization was always completely prevented at the C-4 center, whereas at the C-8 center, it was completely avoided in the case of tyrosine derivatives and considerably diminished for the serine derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.