(R)-2-Benzyloxycarbonylamino-2-methyl-3,3-diphenyl-propionic acid | 281669-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-Benzyloxycarbonylamino-2-methyl-3,3-diphenyl-propionic acid
• 英文别名: (2R)-2-methyl-3,3-diphenyl-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 281669-16-7
• 化学式: C₂₄H₂₃NO₄
• 分子量: 389.451
• InChiKey: ZSPCBVRTCAZHSY-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-Benzyloxycarbonylamino-2-methyl-3,3-diphenyl-propionic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (R)-2-amino-2-methyl-3,3-diphenylpropionic acid
  参考文献：
  名称：

  Synthesis of enantiopure (αMe)Dip and other α-methylated β-branched amino acid derivatives

  摘要：

  This report describes the synthesis of the two enantiomerically pure a-methylated P-branched phenylalanine derivatives, (S)- and (R)-alpha-methyl-beta,beta-diphenylalanine-(alphaMe)Dip-starting from the chiral building blocks (R)- and (S)-N-Boc-N,O-isopropylidene-alpha-methylserine methyl esters, respectively. The key step involves a double alkylation with a Grignard reagent on an ester group. The use of the same protocol for the preparation of other alpha-methylated beta-branched serine derivatives is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00828-5
• 作为产物：
  描述：

  (S)-N-(tert-butoxycarbonyl)-4-(hydroxy(diphenyl)methyl)-2,2,4-trimethyl-1,3-oxazolidine 在 palladium dihydroxide 甲酸 、 jones' reagent 、 氢气 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 60.0 ℃ 、506.62 kPa 条件下， 反应 76.08h， 生成 (R)-2-Benzyloxycarbonylamino-2-methyl-3,3-diphenyl-propionic acid
  参考文献：
  名称：

  Synthesis of enantiopure (αMe)Dip and other α-methylated β-branched amino acid derivatives

  摘要：

  This report describes the synthesis of the two enantiomerically pure a-methylated P-branched phenylalanine derivatives, (S)- and (R)-alpha-methyl-beta,beta-diphenylalanine-(alphaMe)Dip-starting from the chiral building blocks (R)- and (S)-N-Boc-N,O-isopropylidene-alpha-methylserine methyl esters, respectively. The key step involves a double alkylation with a Grignard reagent on an ester group. The use of the same protocol for the preparation of other alpha-methylated beta-branched serine derivatives is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00828-5

文献信息

• Synthesis of enantiopure (αMe)Dip and other α-methylated β-branched amino acid derivatives
  作者：Alberto Avenoza、Jesús H. Busto、Carlos Cativiela、Jesús M. Peregrina、David Sucunza、Marı́a M. Zurbano

  DOI：10.1016/s0957-4166(02)00828-5

  日期：2003.2

  This report describes the synthesis of the two enantiomerically pure a-methylated P-branched phenylalanine derivatives, (S)- and (R)-alpha-methyl-beta,beta-diphenylalanine-(alphaMe)Dip-starting from the chiral building blocks (R)- and (S)-N-Boc-N,O-isopropylidene-alpha-methylserine methyl esters, respectively. The key step involves a double alkylation with a Grignard reagent on an ester group. The use of the same protocol for the preparation of other alpha-methylated beta-branched serine derivatives is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.