(2R,3R)-2-Amino-3-benzyloxy-4-methyl-pentanoic acid | 936001-97-7

• 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: (2R,3R)-2-Amino-3-benzyloxy-4-methyl-pentanoic acid
• CAS: 936001-97-7
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: ACDMGWPQWRCORU-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.55
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-Amino-3-benzyloxy-4-methyl-pentanoic acid 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以89%的产率得到Fmoc-β-OBn-D-Leu-OH
  参考文献：
  名称：

  (−)-Ternatin, a highly N-methylated cyclic heptapeptide that inhibits fat accumulation: structure and synthesis

  摘要：

  A highly N-methylated cyclic heptapeptide, (-)-ternatin, was isolated from the mushroom Coriolus versicolor, which significantly suppressed fat accumulation against 3T3-L1 triurine adipocytes (EC50 = 0.14 mu g/mL). Although ternatin was previously reported to be antibacterial or antimicrobial compound, its inhibitory effect on fat accumulation has been first shown. The structure of (-)-ternatin was revised to be a cyclo [D-allo-Ile(1)-L-(NMe)Ala(2)-L-(NMe)Leu(3)-L-Leu(4)-L-(NMe)Ala(5)-D-(NMe)Ala(6)-(2R,3R)-3-hydroxy-Leu(7)] by spectroscopic analysis and chemical synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.073
• 作为产物：
  描述：

  2,2,2-三氯乙酰胺苄酯 在 palladium on activated charcoal sodium hydroxide 、 三氟甲磺酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (2R,3R)-2-Amino-3-benzyloxy-4-methyl-pentanoic acid
  参考文献：
  名称：

  (−)-Ternatin, a highly N-methylated cyclic heptapeptide that inhibits fat accumulation: structure and synthesis

  摘要：

  A highly N-methylated cyclic heptapeptide, (-)-ternatin, was isolated from the mushroom Coriolus versicolor, which significantly suppressed fat accumulation against 3T3-L1 triurine adipocytes (EC50 = 0.14 mu g/mL). Although ternatin was previously reported to be antibacterial or antimicrobial compound, its inhibitory effect on fat accumulation has been first shown. The structure of (-)-ternatin was revised to be a cyclo [D-allo-Ile(1)-L-(NMe)Ala(2)-L-(NMe)Leu(3)-L-Leu(4)-L-(NMe)Ala(5)-D-(NMe)Ala(6)-(2R,3R)-3-hydroxy-Leu(7)] by spectroscopic analysis and chemical synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.073