(+/-)-threo-2-amino-3-hydroxy-heptanoic acid | 2076-45-1

• 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: (+/-)-threo-2-amino-3-hydroxy-heptanoic acid
• 英文别名: (+/-)-threo-2-Amino-3-hydroxy-heptansaeure；(2S,3R)-2-amino-3-hydroxyheptanoic acid
• CAS: 2076-45-1；2076-59-7；32454-75-4；32454-76-5；50730-81-9；122795-64-6
• 化学式: C₇H₁₅NO₃
• 分子量: 161.201
• InChiKey: HWUNCKBWHUGJNU-RITPCOANSA-N

物化性质

• 熔点：
  222 °C
• 沸点：
  337.5±32.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙醇 、 (+/-)-threo-2-amino-3-hydroxy-heptanoic acid 在 盐酸 作用下， 生成 (+/-)-threo-2-amino-3-hydroxy-heptanoic acid ethyl ester
  参考文献：
  名称：

  Ortin et al., Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica, 1958, vol. 54, p. 209,213

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (2S,3R)-3-hydroxy-2-[[(1S)-2-hydroxy-1-phenylethyl]amino]heptanoate 在 palladium dihydroxide 氢气 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以32 mg的产率得到(+/-)-threo-2-amino-3-hydroxy-heptanoic acid
  参考文献：
  名称：

  Application of enantiopure templated azomethine ylids to β-hydroxy-α-amino acid synthesis

  摘要：

  Chiral stabilised azomethine ylids derived from the reaction of (5S)-5-phenylmorpholin-2-one (1) with aldehydes undergo efficient and highly diastereocontrolled cycloaddition with a second molecule of aldehyde to furnish products (2) which may be converted into enantiomerically pure three (2S,3R) beta-hydroxy-alpha-amino acids (3) in excellent yield, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00302-0

文献信息

• CYCLIC PEPTIDE COMPOUND HAVING HIGH MEMBRANE PERMEABILITY, AND LIBRARY CONTAINING SAME
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP3636807A1

  公开（公告）日：2020-04-15

  The present inventors have found that when screening for cyclic peptide compounds that can specifically bind to a target molecule, the use of a library including cyclic peptide compounds having a long side chain in the cyclic portion can improve the hit rate for cyclic peptide compounds that can specifically bind to the target molecule. Meanwhile, the present inventors have found that tryptophan and tyrosine residues, which have conventionally been used in oral low molecular-weight pharmaceuticals and are amino acid residues having an indole skeleton or a hydroxyphenyl group, are not suitable for peptides intended to attain high membrane permeability.

  本发明人发现，在筛选能与目标分子特异性结合的环肽化合物时，使用包括环状部分具有长侧链的环肽化合物库，可以提高能与目标分子特异性结合的环肽化合物的命中率。同时，本发明者发现色氨酸和酪氨酸残基不适合用于旨在获得高膜渗透性的肽，这两种残基通常用于口服低分子量药物，是具有吲哚骨架或羟基苯基的氨基酸残基。
• Stereoselective Synthesis of <i>Threo</i> and <i>Erythro</i> β-Hydroxy and β-Disubstituted-β-Hydroxy α-Amino Acids
  作者：Mark A. Blaskovich、Ghotas Evindar、Nicholas G. W. Rose、Scott Wilkinson、Yue Luo、Gilles A. Lajoie

  DOI：10.1021/jo972294l

  日期：1998.5.1

  Optically pure N-protected serine aldehyde equivalents can be prepared by the protection of the carboxylic group of serine by a cyclic ortho ester. Alkylation of N-Cbz-, N-Fmoc- or N-Boc-protected serine with oxetane tosylate 1 or bromide 2 gives the corresponding oxetane esters 4a-c which can easily be converted to the cyclic ortho esters 5a-c. A variety of unusual threo beta-hydroxy amino acids have been synthesized by Grignard addition to these optically pure serine aldehyde equivalents. The erythro diastereomers can be obtained by oxidation of the initial three adduct followed by reduction with LiBH4. Also described is a general approach for the diastereoselective synthesis of optically pure beta,beta-dialkyl-beta-hydroxy alpha-amino acids. These highly substituted amino acids are prepared by a sequence of Grignard addition to the optically active serine aldehyde equivalent, followed by oxidation of the initial adduct, and a second Grignard addition to the resulting ketone. The hydroxy adduct is obtained with very high diastereoselectivity (84-96% de). All four diastereomers can be selectively synthesized by varying the order of the Grignard additions and the chirality of the initial synthon. Removal of the protecting groups can be effected in very mild conditions, giving excellent yields of highly substituted amino acids in high diastereomeric purity.
• Stucky, Gerhard; Seebach, Dieter, Chemische Berichte, 1989, vol. 122, p. 2365 - 2376
  作者：Stucky, Gerhard、Seebach, Dieter

  DOI：——

  日期：——
• Ortin et al., Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica, 1959, vol. 55, p. 163,164,169
  作者：Ortin et al.

  DOI：——

  日期：——
• Ortin et al., Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica, <hi>1958</hi>, vol. 54, p. 209,213
  作者：Ortin et al.

  DOI：——

  日期：——