methyl (2R,3S)-2-hydroxy-3-methylpentanoate | 56577-29-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2R,3S)-2-hydroxy-3-methylpentanoate
• CAS: 56577-29-8
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: OQXGUAUSWWFHOM-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-2-hydroxy-3-methylpentanoate 在 吡啶 、 lithium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 102.0h， 生成 (2R,3S)-2-[(2S)-2-[tert-butyl(dimethyl)silyl]oxy-3-methylbutanoyl]oxy-3-methylpentanoic acid
  参考文献：
  名称：

  丙二酰胺的全合成和立体化学重分配

  摘要：

  丙二酰胺的首次全合成，这是从Lyngbya sp。的海洋蓝细菌组合中分离出的一种无环肽。该合成导致的重新分配同种异体- ð maedamide的-Ile是升-Ile，其通过支持1 H和13个C NMR数据。

  DOI：

  10.1016/j.tetlet.2015.06.090
• 作为产物：
  描述：

  D-别异亮氨酸 在 硫酸 、 sodium nitrite 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 17.08h， 生成 methyl (2R,3S)-2-hydroxy-3-methylpentanoate
  参考文献：
  名称：

  Lipodiscamides A–C, New Cytotoxic Lipopeptides from Discodermia kiiensis

  摘要：

  Lipodiscamides A-C, three new lipodepsipeptides, were characterized from the marine sponge Discodermia kiiensis. These structurally rare cyclic lipodepsipeptides were found to possess an unprecedented dilactone macrocycle and, thus, represent a new family of lipopeptides. They are the only lipopeptides bearing 4S-hydroxy-trans-2-enoate, and noncanonical amino acids, l-3-ureidoalanine (Uda), E-dehydronorvaline (Denor), and d-citrulline (Cit). MTT assays against P388 and HeLa cells revealed the moderate cytotoxicity of all three compounds.

  DOI：

  10.1021/ol501271v

文献信息

• Facile synthesis of amino acid-derived novel chiral hypervalent iodine(V) reagents and their applications
  作者：Yasushi Yoshida、Akina Magara、Takashi Mino、Masami Sakamoto

  DOI：10.1016/j.tetlet.2016.10.016

  日期：2016.11

  Amino acid-derived novel chiral hypervalent iodine(V) reagents were synthesized from the corresponding chiral iodoarenes through DMDO oxidations. Their oxidation states were determined by the 13C NMR chemical shifts of the ipso-carbon of the iodine atom, HRMS analysis, and elemental analyses. They were applied to the enantioselective hydroxylative dearomatization/[4+2]-dimerization cascade reactions

  从相应的手性碘芳烃通过DMDO氧化合成了氨基酸衍生的新型手性高价碘试剂。它们的氧化态由碘原子的ipso-碳的13 C NMR化学位移，HRMS分析和元素分析确定。将它们用于苯酚衍生物的对映选择性羟基化脱芳香化/ [4 + 2]-二聚级联反应，得到所需产物，其ee最高为58％。
• Process for the preparation of azide derivatives
  申请人：Eisai Co., Ltd.

  公开号：US05986088A1

  公开（公告）日：1999-11-16

  A process for the preparation of azide derivatives useful as drugs, perfumes or intermediates of dyes by reacting an alcohol derivative with di-p-nitrophenyl phosphorazidate in the presence of 1,8-diazabicyclo[5.4.0]-7-undecene.

  一种制备偶氮衍生物的方法，可用作药物、香料或染料中间体，通过在1,8-二氮杂双环[5.4.0]-7-十一烯存在下，将醇衍生物与二对硝基苯磷酰叠氮酸酯反应。
• Total Synthesis of L-156,373 and an oxoPiz Analogue via a Submonomer Approach
  作者：Yassin M. Elbatrawi、Chang Won Kang、Juan R. Del Valle

  DOI：10.1021/acs.orglett.8b00912

  日期：2018.5.4

  The first chemical synthesis of L-156,373 (1), a potent oxytocin receptor antagonist isolated from Streptomyces silvensis, is reported. Assembly of the unusual d-Piz-l-Piz dipeptide subunit was achieved through a sequential electrophilic amination–acylation–deprotection strategy followed by late-stage Piz ring formation. Synthesis and incorporation of a novel N-hydroxy-l-isoleucine building block is

  报道了从银链霉菌中分离出的一种强效催产素受体拮抗剂L-156,373（1）的第一个化学合成方法。组件中的异常的d -Piz-升-Piz二肽亚单位通过连续的电胺化酰化脱保护策略来实现，随后后期的Piz环的形成。还描述了新型N-羟基-1-异亮氨酸结构单元的合成和掺入。将该亚单体方法进一步应用于从Fmoc-Glu（t Bu）-OH构件开始的1的二-δ-氧代哌嗪酸类似物的合成。
• Oxetanyl Amino Acids for Peptidomimetics
  作者：Guido P. Möller、Steffen Müller、Bernd T. Wolfstädter、Susanne Wolfrum、Dirk Schepmann、Bernhard Wünsch、Erick M. Carreira

  DOI：10.1021/acs.orglett.7b00745

  日期：2017.5.19

  Peptides are important in the drug discovery process. In analogy to nonpeptidic small-molecule counterparts, they can sometimes suffer from disadvantages such as their low bioavailability and poor metabolic stability. Herein, we report the synthesis of new oxetanyl dipeptides and their incorporation into Leu-enkephalin analogues as proof-of-principle studies. The modular approach that is described enables the incorporation of a variety of oxetanyl amino acids into potential peptide therapeutics.
• An efficient synthesis of the C27–C45 fragment of lagunamide A, a cyclodepsipeptide with potent cytotoxic and antimalarial properties
  作者：Hui-Ming Liu、Chieh-Yu Chang、Ya-Chi Lai、Mei-Due Yang、Ching-Yao Chang

  DOI：10.1016/j.tetasy.2013.11.020

  日期：2014.1

  An efficient and stereoselective synthesis of the entire C27-C45 moiety of lagunamide A has been achieved from 1-[(4S)-4-benzyl-2-thioxothiazolidin-3-yl]propan-1-one in six steps with 22% overall yield. The key step in the synthesis is an asymmetric acetal aldol reaction featuring the enantioselective addition of a chiral thiazolidinethione-derived titanium enolate to an acetal to establish the stereochemistry at C39. (C) 2013 Elsevier Ltd. All rights reserved.