(2S,5S)-5-hydroxylysine hydrochloride | 108691-35-6

• 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: (2S,5S)-5-hydroxylysine hydrochloride
• 英文别名: L_S-threo-5-hydroxy-lysine ; hydrochloride；L_S-threo-5-Hydroxy-lysin; Hydrochlorid；erythro-5-Hydroxy-L-lysine monohydrochloride；(2S,5S)-2,6-diamino-5-hydroxyhexanoic acid;hydrochloride
• CAS: 108691-35-6
• 化学式: C₆H₁₄N₂O₃*ClH
• 分子量: 198.65
• InChiKey: MJXVOTKVFFAZQJ-FHAQVOQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.08
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,5S)-5-hydroxylysine hydrochloride 在 氯化亚砜 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 56.0h， 生成 methyl (2S,5S)-2,6-bis((tert-butoxycarbonyl)amino)-5-hydroxyhexanoate
  参考文献：
  名称：

  Synthesis of l-aminohomohistidine (l-Ahh)

  摘要：

  A short Synthesis Of L-aminohomohistidine (L-Ahh) is described, which starts from readily available delta-hydroxy-L-lysine. The embedding of the basic guanidino Moiety in the aromatic imidazole lowers the basicity of the side chain to a pK(a), of 8.3. It is proposed that L-Ahh may be employed as an arginine-mimetic in medicinal chemistry. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.027
• 作为产物：
  描述：

  tert-butyl (3S,5S,6R)-3-[(3S)-4-azido-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate 在 palladium on activated charcoal 三氟乙酸 、 盐酸 、 氢气 作用下， 以 水 、 甲醇 为溶剂， 反应 25.0h， 以78%的产率得到(2S,5S)-5-hydroxylysine hydrochloride
  参考文献：
  名称：

  A practical and simple synthesis of (2S,5R)- and (2S,5S)-5-hydroxylysine and of a related α-amino acid required for the synthesis of the collagen cross-link pyridinoline

  摘要：

  A four step synthesis of (2S,5R)- and (2S,5S)-5-hydroxylysine using Williams' glycine template methodology for controlling the stereogenicity at the alpha-position is reported. This route offers the possibility for the synthesis of all possible isomers of 5-hydroxylysine and of an important alpha-amino acidic iodohydrin required for the construction of the hydroxylated side chain of the collagen cross-link pyridinoline. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.004

文献信息

• A practical and simple synthesis of (2S,5R)- and (2S,5S)-5-hydroxylysine and of a related α-amino acid required for the synthesis of the collagen cross-link pyridinoline
  作者：Pietro Allevi、Mario Anastasia

  DOI：10.1016/j.tetasy.2004.06.004

  日期：2004.7

  A four step synthesis of (2S,5R)- and (2S,5S)-5-hydroxylysine using Williams' glycine template methodology for controlling the stereogenicity at the alpha-position is reported. This route offers the possibility for the synthesis of all possible isomers of 5-hydroxylysine and of an important alpha-amino acidic iodohydrin required for the construction of the hydroxylated side chain of the collagen cross-link pyridinoline. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of l-aminohomohistidine (l-Ahh)
  作者：Manuel Friedel、Thomas Lindel

  DOI：10.1016/j.tetlet.2004.02.027

  日期：2004.3

  A short Synthesis Of L-aminohomohistidine (L-Ahh) is described, which starts from readily available delta-hydroxy-L-lysine. The embedding of the basic guanidino Moiety in the aromatic imidazole lowers the basicity of the side chain to a pK(a), of 8.3. It is proposed that L-Ahh may be employed as an arginine-mimetic in medicinal chemistry. (C) 2004 Elsevier Ltd. All rights reserved.