(S)-2-amino-6-hydroxy-hexanoic acid methyl ester | 167090-40-6

• 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: (S)-2-amino-6-hydroxy-hexanoic acid methyl ester
• 英文别名: methyl (2S)-2-amino-6-hydroxyhexanoate
• CAS: 167090-40-6
• 化学式: C₇H₁₅NO₃
• 分子量: 161.201
• InChiKey: TYGJRVXIEXIONP-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-6-hydroxy-hexanoic acid methyl ester 在 N-甲基吗啉 、 草酰氯 、 magnesium sulfate 、 二甲基亚砜 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 3.17h， 生成 [S(R*,R*)]-1-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,2,3,4-tetrahydro-2-pyridinecarboxylicacid, methyl ester
  参考文献：
  名称：

  Process Development in the Synthesis of the ACE Intermediate MDL 28,726

  摘要：

  MDL 28,726 is a key intermediate in the synthesis of the ACE inhibitors MDL 27,210A and MDL 100,240, An efficient nine-step synthesis of this tricyclic acid, which has three chiral centers, was developed beginning with 3,4-dihydro-2H-pyran. A key step in the synthesis features an enzyme-catalyzed resolution of the lithium salt of the N-trifluoroacetamide of (R,S)-6-hydroxynorleucine. All of the steps were optimized and completed in reactor equipment using environmentally acceptable processes. Process development of this route is described.

  DOI：

  10.1021/op970125x
• 作为产物：
  描述：

  6-hydroxynorleucine lithium salt 在 盐酸 、 Acylase I 、 lithium hydrochloride monohydrate 、 水 、 lithium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 正丁醇 为溶剂， 反应 13.67h， 生成 (S)-2-amino-6-hydroxy-hexanoic acid methyl ester
  参考文献：
  名称：

  Process Development in the Synthesis of the ACE Intermediate MDL 28,726

  摘要：

  MDL 28,726 is a key intermediate in the synthesis of the ACE inhibitors MDL 27,210A and MDL 100,240, An efficient nine-step synthesis of this tricyclic acid, which has three chiral centers, was developed beginning with 3,4-dihydro-2H-pyran. A key step in the synthesis features an enzyme-catalyzed resolution of the lithium salt of the N-trifluoroacetamide of (R,S)-6-hydroxynorleucine. All of the steps were optimized and completed in reactor equipment using environmentally acceptable processes. Process development of this route is described.

  DOI：

  10.1021/op970125x

文献信息

• Macrocyclic cysteine protease inhibitors and compositions thereof
  申请人：Lincoln University

  公开号：US09434762B2

  公开（公告）日：2016-09-06

  The present invention provides a novel class of macrocyclic compounds, which are useful as cysteine protease inhibitors. Also provided are novel intermediates and methods of preparing the compounds. The invention also provides pharmaceutical compositions comprising the compounds. The compounds and compositions are useful in methods of treating or preventing one or more diseases associated with cysteine protease activity, particularly those associated with calpain activity.

  本发明提供了一类新型的大环化合物，这些化合物可用作半胱氨酸蛋白酶抑制剂。还提供了新颖的中间体和制备这些化合物的方法。该发明还提供了包含这些化合物的药物组合物。这些化合物和组合物可用于治疗或预防与半胱氨酸蛋白酶活性相关的一种或多种疾病，特别是与钙蛋白酶活性相关的疾病。
• Macrocyclic Cysteine Protease Inhibitors and Compositions Thereof
  申请人：Abell Andrew David

  公开号：US20110021434A1

  公开（公告）日：2011-01-27

  The present invention provides a novel class of macrocyclic compounds, which are useful as cysteine protease inhibitors. Also provided are novel intermediates and methods of preparing the compounds. The invention also provides pharmaceutical compositions comprising the compounds. The compounds and compositions are useful in methods of treating or preventing one or more diseases associated with cysteine protease activity, particularly those associated with calpain activity.

  本发明提供了一类新型的大环化合物，可用作半胱氨酸蛋白酶抑制剂。还提供了新型中间体和制备这些化合物的方法。该发明还提供了包含这些化合物的药物组合物。这些化合物和组合物可用于治疗或预防与半胱氨酸蛋白酶活性有关的一种或多种疾病，特别是与钙蛋白酶活性有关的疾病。
• SYNTHESIS OF (<i>S</i>)-(−)-1-[(9-FLUORENYLMETHOXYCARBONYL)AMINO-5-CARBOXYPENTYL]-3-HYDROXYPYRIDINIUM TRIFLUOROACETATE
  作者：Maciej Adamczyk、Rajarathnam E. Reddy

  DOI：10.1080/00304940009355922

  日期：2000.6

  Derivatives of (X)-(-)1-(amino-5-carboxypentyl]-3-hydroxypyridinium salt 1 are present in bone collagen and play an important role in maintaining the integrity of this tissue.’.’ The synthesis of racemic (k)-l starting from tert-butyl-(2-tert-butoxycarbonyl)amino acetate has been reported previously.’ We present here the preparation of an important chiral building block, 0)-(-)-Fmoc derivative of 1 (compound

  (X)-(-)1-(amino-5-carboxypentyl]-3-hydroxypyridinium salt 1 的衍生物存在于骨胶原中，在维持该组织的完整性方面起着重要作用。'.' 外消旋 ( k)-l 从叔丁基-(2-叔丁氧基羰基) 氨基乙酸酯开始已有报道。' 我们在此介绍了一种重要的手性结构单元的制备，0)-(-)-Fmoc 衍生物 1（化合物2)，需要通过固相技术合成包含胶原蛋白的肽。因此，由Na-叔-Boc-赖氨酸制备的(S)-(-)-甲基2-[(叔丁氧基羰基)氨基]-6-羟基戊酸酯(3)？用三氟乙酸在二氯甲烷中水解，得到 (S)-胺 (4)，无需纯化，用氯甲酸 9-芴基甲酯 5 处理，以 65% 的收率得到 (S)-(-)-甲基 2-[(9-芴基甲氧基羰基) 氨基]-6 羟基戊酸酯 (5)。使用碘、三苯基膦和咪唑将 (9 -5 中的羟基官能团转化为相应的碘化物 (S)-(+)-6，产率为
• AMINO ACID DERIVATIVE
  申请人：Eisai Co., Ltd.

  公开号：EP0671172A1

  公开（公告）日：1995-09-13

  An amino acid derivative having an angiotensin I-converting enzyme inhibitor activity, a vasopressin antagonism and an atrial natriuretic peptide hydrolase inhibitor activity, and represented by general formula (I) wherein R¹ represents hydrogen or acyl; R² represents hydrogen, lower alkyl, cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted arylalkyl or optionally substituted heteroarylalkyl; m and n represent each independently an integer of 0.1 or 2; and J represents a cyclic group having an angiotensin I-converting enzyme inhibitor activity.

  一种具有血管紧张素Ⅰ转换酶抑制剂活性、血管加压素拮抗剂活性和心房钠尿肽水解酶抑制剂活性的氨基酸衍生物，由通式(I)表示 其中R¹代表氢或酰基；R²代表氢、低级烷基、环烷基、任选取代的芳基、任选取代的杂芳基、任选取代的芳烷基或任选取代的杂芳基烷基；m和n各自独立地代表0.1或2的整数；J代表具有血管紧张素I-转化酶抑制剂活性的环状基团。
• A novel three-step hydroxy-deamination sequence: Conversion of lysine to 6-hydroxynorleucine derivatives
  作者：C.Richard Nevill、Paul T. Angell

  DOI：10.1016/s0040-4039(98)01142-3

  日期：1998.8

  Oxidation of carbamates with catalytic RuO4, generated from RuO4, and NaBrO3, provides the corresponding acyl carbamates, which can be reduced with NaBH4 to provide alcohols. Application of this methodology to L-lysine provides (S)-6-hydroxynorleucine derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.