6-hydroxypiperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester | 1025782-34-6

• 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: 6-hydroxypiperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
• 英文别名: 1-O-tert-butyl 2-O-methyl (2S)-6-hydroxypiperidine-1,2-dicarboxylate
• CAS: 1025782-34-6
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: UMASOLDPFPVAHB-IENPIDJESA-N

物化性质

• 沸点：
  352.1±42.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-hydroxypiperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-叔丁氧羰基-DL-哌啶酸甲酯
  参考文献：
  名称：

  高度化学选择性还原N-Boc保护的内酰胺

  摘要：

  N-Boc保护的内酰胺可在其他基团（例如酯，腈，氨基甲酸酯或双键）存在下进行化学选择性还原，方法是先使用三乙基硼氢化锂将酰胺羰基还原为相应的缩醛，然后再用三乙基硅烷/三氟化硼醚化物。该方法保留了底物中存在的手性。

  DOI：

  10.1016/s0040-4039(00)73047-4
• 作为产物：
  描述：

  (-)-(S)-6-oxo-2-piperidinecarboxylic acid methyl ester 在 4-二甲氨基吡啶 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 7.83h， 生成 6-hydroxypiperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
  参考文献：
  名称：

  A Total Synthesis of Nannochelin A. A Short Route to Optically Active N^ω-Hydroxy-α-amino Acid Derivatives

  摘要：

  The total synthesis of nannochelin A, a lysine-basd cinnamoyl hydroxamate produced by Nannocystis exedens, is described. The key transformation involves construction of the N-epsilon-cinnamoyl-N-epsilon-hydroxy-L-lysine methyl ester fragment by partial reduction of the lactam carbonyl of 6 derived from L-lysine, oximation of this aldehyde equivalent compound 8 with O-[2-(trimethylsilyl)ethyl]hydroxylamine, and reduction of the oxime 10, followed by N-acylation prior to coupling with the external carbonyls of citric acid. This methodology will be applicable to synthesis of other hydroxamate-containing siderophores bearing hydrogenolyzable groups in the molecule.

  DOI：

  10.1021/jo961458f

文献信息

• [EN] NOVEL INTERLEUKIN-1beta CONVERTING ENZYME INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS D'ENZYMES DE CONVERSION DE L'INTERLEUKINE 1 DOLLAR G(B)
  申请人：PROCTER & GAMBLE

  公开号：WO2003104231A1

  公开（公告）日：2003-12-18

  The present invention relates to novel compounds, compositions comprising said compounds, and uses thereof, said compounds having the formula (a). X is -CH2-, -O- or -NR9-;R is a carbocyclic or heterocyclic ring;R1 is a cysteine trap;R2a, R2a', R2b, and R2b' are each independently hydrogen, C1-C4 alkyl, C1-C4 alkoxy, and mixtures thereof; or R2a' and R2b' can taken together to form a double bond; R9 is hydrogen or a unit having the formula -L2-R10; L is the same as defined herein above; R10 is hydrogen; substituted or unsubstituted C1-C6 linear; branched, or cyclic hydrocarbyl; substituted or unsubstituted aryl; substituted or unsubstituted C1-C9 heterocyclic; and substituted or unsubstituted heteroaryl.

  本发明涉及新化合物、包含所述化合物的组合物以及它们的用途，所述化合物具有以下式（a）。X为-CH2-、-O-或-NR9-；R为碳环或杂环；R1为半胱氨酸陷阱；R2a、R2a'、R2b和R2b'分别独立地为氢、C1-C4烷基、C1-C4烷氧基及它们的混合物；或者R2a'和R2b'可以共同形成双键；R9为氢或具有以下式-L2-R10的单元；L与上文中定义的相同；R10为氢；取代或未取代的C1-C6线性、支链或环烃基；取代或未取代的芳基；取代或未取代的C1-C9杂环基；以及取代或未取代的杂芳基。
• [EN] STAT MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS DE STAT ET LEURS UTILISATIONS
  申请人：[en]RECLUDIX PHARMA, INC.

  公开号：WO2023133336A1

  公开（公告）日：2023-07-13

  Provided are compounds of Formula (I): and pharmaceutically acceptable salts and compositions thereof, which are useful for treating a variety of conditions associated with STAT3 and/or STAT6.
• Highly chemoselective reduction of N-Boc protected lactams
  作者：Concepción Pedregal、Jesús Ezquerra、Ana Escribano、M.Carmen Carreño、José L. García Ruano

  DOI：10.1016/s0040-4039(00)73047-4

  日期：1994.3

  N-Boc protected lactams can be reduced chemoselectively in the presence of other groups such as esters, nitriles, carbamates or double bonds by first reducing the amide carbonyl group into the corresponding hemiaminal using lithium triethylborohydride followed by further reduction of the hemiaminal intermediate with triethylsilane/Boron trifluoride etherate. This method preserves the chirality present

  N-Boc保护的内酰胺可在其他基团（例如酯，腈，氨基甲酸酯或双键）存在下进行化学选择性还原，方法是先使用三乙基硼氢化锂将酰胺羰基还原为相应的缩醛，然后再用三乙基硅烷/三氟化硼醚化物。该方法保留了底物中存在的手性。
• A Total Synthesis of Nannochelin A. A Short Route to Optically Active <i>N</i>^ω-Hydroxy-α-amino Acid Derivatives
  作者：Takeshi Sakamoto、Hao Li、Yasuo Kikugawa

  DOI：10.1021/jo961458f

  日期：1996.1.1

  The total synthesis of nannochelin A, a lysine-basd cinnamoyl hydroxamate produced by Nannocystis exedens, is described. The key transformation involves construction of the N-epsilon-cinnamoyl-N-epsilon-hydroxy-L-lysine methyl ester fragment by partial reduction of the lactam carbonyl of 6 derived from L-lysine, oximation of this aldehyde equivalent compound 8 with O-[2-(trimethylsilyl)ethyl]hydroxylamine, and reduction of the oxime 10, followed by N-acylation prior to coupling with the external carbonyls of citric acid. This methodology will be applicable to synthesis of other hydroxamate-containing siderophores bearing hydrogenolyzable groups in the molecule.