(R)-2-amino-3-hydroxy-2,3-dimethylbutyric acid | 81107-70-2

• 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-amino-3-hydroxy-2,3-dimethylbutyric acid
• 英文别名: (2R)-2,3,3-Trimethylserin；3-Hydroxy-3-methyl-D-isovaline；(2R)-2-amino-3-hydroxy-2,3-dimethylbutanoic acid
• CAS: 81107-70-2
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: XRTPVBDGIHBVJI-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-N-(tert-butoxycarbonyl)-4-(1-hydroxy-1-methylethyl)-2,2,4-trimethyloxazolidine 在 palladium on activated charcoal 盐酸 、 jones' reagent 、 氢气 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 57.08h， 生成 (R)-2-amino-3-hydroxy-2,3-dimethylbutyric 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

• Schoellkopf, Ulrich; Groth, Ulrich; Hartwig, Wolfgang, Liebigs Annalen der Chemie, 1981, # 12, p. 2407 - 2418
  作者：Schoellkopf, Ulrich、Groth, Ulrich、Hartwig, Wolfgang

  DOI：——

  日期：——
• 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.