Boc-(4S,5S)-4-hydroxy-pyrrolidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: Boc-(4S,5S)-4-hydroxy-pyrrolidin-2-one
• 英文别名: (4S,5S)-4-hydroxy-5-isobutyl-1-t-butoxycarbonylpyrrolidin-2-one；(4S,5S)-4-hydroxy-5-isobutyl-1-tert-butoxycarbonylpyrrolidin-2-one；(4S,5S)-4-hydroxy-5-isobutyl-1-t-butoxycarbonyl-2-pyrrolidinone；(S,S)-1-tert-butoxycarbonyl-4-hydroxy-5-isobutyl-2-pyrrolidinone；tert-butyl (2S,3S)-3-hydroxy-2-(2-methylpropyl)-5-oxopyrrolidine-1-carboxylate
• 化学式: C₁₃H₂₃NO₄
• 分子量: 257.33
• InChiKey: HYAQUMODGYTCDT-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Boc-(4S,5S)-4-hydroxy-pyrrolidin-2-one 在 caesium carbonate 作用下， 以 甲醇 为溶剂， 以87%的产率得到(3S,4S)-methyl 3-hydroxy-6-methyl-4-t-butoxycarbonylamino-heptanoate
  参考文献：
  名称：

  Lewis acid-promoted direct substitution of 4-methoxy- and 4-phenylthio-2-oxazolidinones by alkyl cuprates. Facile preparation of (3s,4s)-statine and (3s,4s)-cyclohexylstatine.

  摘要：

  Treatment of 4-methoxy- and 4-phenylthio-2-oxazolidinones with a combination of cuprates and BF3 results in smooth formation of 4-alkyl and 4-aryl derivatives in high yield. By this method, the titled compounds of biological interest are readily synthesized from (4S,5S)-5-allyl-4-methoxy (or 4-phenylthio)-2-oxazolidinones stereoselectively.

  DOI：

  10.1016/0040-4039(91)80822-n
• 作为产物：
  描述：

  2-甲基-2-丙基[(2S)-4-甲基-1-氧代-2-戊烷基]氨基甲酸酯 在 四氯化钛 二甲基硫 、 对甲苯磺酸 、 臭氧 、 pyridinium chlorochromate 、 dibenzylammonium trifluoroacetate 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 12.41h， 生成 Boc-(4S,5S)-4-hydroxy-pyrrolidin-2-one
  参考文献：
  名称：

  通过缩醛模板的不对称合成。14. 1对映体纯的（3 S，4 S）-和（3 S，4 R）-Statine衍生物的制备

  摘要：

  通过亲核试剂攻击结晶的差向异构N-BOC-内酰胺7a和7b，已经制备了几种（3S，4S）-和（3S，4R）-Statine衍生物。内酰胺合成的关键步骤是TiCl 4催化的由（R）-1,3-丁二醇衍生的缩醛与烯丙基三甲基硅烷的偶联反应。

  DOI：

  10.1016/s0040-4039(00)96906-5

文献信息

• A novel Wittig reaction of oxazolidinones: Stereospecific synthesis of N-BOC-(3S,4S)-Statine and N-BOC-(3S,4S)-AHPPA
  作者：G.Vidyasagar Reddy、G.Venkat Rao、D.S. Iyengar

  DOI：10.1016/s0040-4039(98)02409-5

  日期：1999.1

  Stereospecific synthesis of N-BOC-(3S,4S)-Statine and N-BOC-(3S,4S)-AHPPA is achieved via a novel Wittig reaction of oxazolidinones in an efficient manner.

  N-BOC-（3 S，4 S）-Statine和N-BOC-（3 S，4 S）-AHPPA的立体定向合成是通过恶唑烷酮的新型Wittig反应以有效方式实现的。
• Synthesis of statine from (S)-malic acid; stereocontrol via radical cyclization
  作者：Wim-Jan Koot、Roel van Ginkel、Mirko Kranenburg、Henk Hiemstra、Saskia Louwrier、Marinus J. Moolenaar、W.Nico Speckamp

  DOI：10.1016/s0040-4039(00)92639-x

  日期：1991.1

  Highly stereoselective syntheses of enantiomerically pure γ-amino acids statine and 4-epi-statine from (S)-malic acid are described by using, respectively, an intramolecular α-acylamino radical reaction and an intermolecular N-acyliminium allylsilane coupling.

  （S）-苹果酸对映体纯的γ-氨基酸他汀和4-表位他汀的高度立体选择性合成分别通过分子内α-酰基氨基自由基反应和分子间N-酰基丙烯基硅烷偶联来描述。
• Synthesis of chiral urethane N-alkoxycarbonyl tetramic acids from urethane N-carboxyanhydrides (UNCAs)
  作者：Jean-Alain Fehrentz、Elisabeth Bourdel、Jean-Christophe Califano、Olivier Chaloin、Chantal Devin、Patrick Garrouste、Ana-Christina Lima-Leite、Muriel Llinares、François Rieunier、Jean Vizavonna、François Winternitz、Albert Loffet、Jean Martinez

  DOI：10.1016/s0040-4039(00)76757-8

  日期：1994.3

  The synthesis of chiral N-protected tetramic acid derivatives which are important precursors of β-hydroxy γ-amino acid under mild conditions is described. Reaction of urethane-N-carboxyanhydrides (UNCAs) with Meldrum's acid in the presence of a tertiary amine, followed by subsequent cyclisation produced tetramic acid derivatives. This procedure is applicable to Boc-, Fmoc- and Z- N-carboxyanhydrides

  描述了在温和条件下手性N-保护的四酸衍生物的合成，该衍生物是β-羟基γ-氨基酸的重要前体。在叔胺存在下，氨基甲酸酯-N-羧基酐（UNCA）与Meldrum酸反应，然后环化生成四甲酸衍生物。此程序适用于Boc-，Fmoc-和Z- N-羧基酸酐。
• Process for the stereospecific preparation of
  申请人：Propeptide

  公开号：US05498732A1

  公开（公告）日：1996-03-12

  The invention relates to a process for the preparation of 5-(1-hydroxy-2-urethanethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives, which are precursors of chiral tetramic acid derivatives. According to this process, an N-urethane-protected .alpha.-amino acid N-carboxy-anhydride is reacted with Meldrum's acid in an inert organic solvent medium in the presence of a tertiary amine. This process makes it possible to conserve the chirality of the starting material and in particular to simplify the synthesis of 4-amino-3-hydroxy acids and the derivatives thereof via the tetramic acid route.

  本发明涉及一种制备5-(1-羟基-2-脲乙基亚甲基)-2,2-二甲基-1,3-二氧杂环戊-4,6-二酮衍生物的方法，该衍生物是手性四元酸衍生物的前体。根据该方法，在惰性有机溶剂介质中，在三级胺的存在下，将N-脲保护的α-氨基酸N-羧酸酐与梅尔德鲁姆酸反应。该方法使得起始物的手性得以保留，特别是通过四元酸途径简化合成4-氨基-3-羟基酸及其衍生物的方法。
• Symplocin A, a Linear Peptide from the Bahamian Cyanobacterium<i>Symploca</i>sp. Configurational Analysis of<i>N</i>,<i>N</i>-Dimethylamino Acids by Chiral-Phase HPLC of Naphthacyl Esters
  作者：Tadeusz F. Molinski、Kirk A. Reynolds、Brandon I. Morinaka

  DOI：10.1021/np200861n

  日期：2012.3.23

  The absolute stereostructures of the components of symplocin A (3), a new N,N-dimethyl-terminated peptide from the Bahamian cyanobacterium Symploca sp., were assigned from spectroscopic analysis, including MS, 2D NMR, and Marfey's analysis. The complete absolute configuration of symplocin A, including the unexpected D-configurations of the terminal N,N-dimethylisoleucine and valic acid residues, was assigned by chiral-phase HPLC of the corresponding 2-naphthacyl esters, a highly sensitive, complementary strategy for assignment of N-blocked peptide residues where Marfey's method is ineffectual or other methods fall short. Symplocin A exhibited potent activity as an inhibitor of cathepsin E (IC50 300 pM).