(2S,3R)-3-hydroxy-L-glutamic acid hydrochloride | 95715-93-8

• 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,3R)-3-hydroxy-L-glutamic acid hydrochloride
• 英文别名: threo-β-hydroxy-L-glutamic acid hydrochloride；threo-β-HGA；L_S-threo-3-hydroxy-glutamic acid ; hydrochloride；L_S-threo-3-Hydroxy-glutaminsaeure; Hydrochlorid；(2S,3R)-2-amino-3-hydroxypentanedioic acid;hydrochloride
• CAS: 95715-93-8
• 化学式: C₅H₉NO₅*ClH
• 分子量: 199.591
• InChiKey: SKBFPHNPXPKPPX-ZVYNFJQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.34
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  121
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  氯甲酸苄酯 、 (2S,3R)-3-hydroxy-L-glutamic acid hydrochloride 在 碳酸氢钠 作用下， 生成 Dl-threo-N-benzyloxycarbonyl-3-hydroxy-glutaminsaeure
  参考文献：
  名称：

  Kamiya,T., Chemical and pharmaceutical bulletin, 1969, vol. 17, # 5, p. 890 - 894

  摘要：

  DOI：
• 作为产物：
  描述：

  ((4R,5R)-4-Hydroxymethyl-2-oxo-oxazolidin-5-yl)-acetic acid methyl ester 在 盐酸 、 jones reagent 作用下， 生成 (2S,3R)-3-hydroxy-L-glutamic acid hydrochloride
  参考文献：
  名称：

  Giovanni, Maria Cristina Di; Misiti, Domenico; Zappia, Giovanni, Gazzetta Chimica Italiana, 1997, vol. 127, # 9, p. 475 - 482

  摘要：

  DOI：

文献信息

• <scp>d</scp>-Glucose based syntheses of β-hydroxy derivatives of <scp>l</scp>-glutamic acid, <scp>l</scp>-glutamine, <scp>l</scp>-proline and a dihydroxy pyrrolidine alkaloid
  作者：K. S. Ajish Kumar、Subrata Chattopadhyay

  DOI：10.1039/c5ra01340b

  日期：——

  The β-hydroxy derivatives of l-glutamic acid, l-glutamine and l-proline, useful for peptide/protein studies, were synthesized starting from d-glucose.

  β-羟基衍生物的L-谷氨酸、L-谷氰酸和L-脯氨酸，可用于肽/蛋白质研究，从D-葡萄糖开始合成。
• Dell'Uomo, Natalina; Giovanni, Maria C. Di; Misiti, Domenico, Liebigs Annalen der Chemie, 1994, # 6, p. 641 - 644
  作者：Dell'Uomo, Natalina、Giovanni, Maria C. Di、Misiti, Domenico、Zappia, Giovanni、Monache, Giuliano Delle

  DOI：——

  日期：——
• Versatile chiral synthons for vic-amino alcohols. Facile synthesis of (2S,3R)-3-hydroxyglutamic acid and (+)-statine
  作者：Takehisa Kunieda、Tadao Ishizuka、Tsunehiko Higuchi、Masaaki Hirobe

  DOI：10.1021/jo00249a055

  日期：1988.7
• Efficient and stereoselective synthesis of threo-β-hydroxy-l-glutamic acid via a tandem (Z)-olefination-conjugate addition
  作者：Hyeonjeong Kim、Dongwon Yoo、Seah Kwon、Young Gyu Kim

  DOI：10.1016/j.tetasy.2009.11.023

  日期：2009.12

  threo-beta-Hydroxy-L-glutamic acid I is an attractive target as a biologically active compound and as a chiral synthon. The required beta-hydroxyl group in 1 was efficiently and stereoselectively introduced via an intramolecular conjugate addition of the N-hydroxymethyl group of gamma-amino-alpha,beta-unsaturated (Z)-ester 4. While the corresponding (E)-ester 3 gave a lower selectivity of ca. 5:1 in the intramolecular conjugate addition, a selectivity of up to 70:1 was shown with (Z)-ester 4. The tandem (Z)-olefination-conjugate addition could be achieved by simply changing the reaction conditions to give a selectivity of >20:1. Thus, the target compound I was obtained as its hydrochloride salt in 70% overall yield over four steps from lactol 2. (C) 2009 Elsevier Ltd. All rights reserved.
• Kamiya,T., Chemical and pharmaceutical bulletin, 1969, vol. 17, # 5, p. 890 - 894
  作者：Kamiya,T.

  DOI：——

  日期：——