(S,S)-piperidinedicarboxylic acid dimethyl ester | 88817-76-9

• 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,S)-piperidinedicarboxylic acid dimethyl ester
• 英文别名: dimethyl (2S)-piperidine-1,2-dicarboxylate
• CAS: 88817-76-9
• 化学式: C₉H₁₅NO₄
• 分子量: 201.222
• InChiKey: YCRKYHORPQVAND-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S,S)-piperidinedicarboxylic acid dimethyl ester 在 sodium tetrahydroborate 、 溴 、 sodium methylate 、 potassium acetate 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 生成 (3S,4R,6S)-2,3,4-triacetoxy-1-aza-8-oxabicyclo[4.3.0]nonan-9-one
  参考文献：
  名称：

  Stereoselective synthesis of azasugars by electrochemical oxidation

  摘要：

  A new method using electrochemical oxidation has been exploited for the stereoselective synthesis of 2,3,6-trihydroxylated 5S-piperidine derivatives. The electrochemical method was Successively used for the conversion of N-protected piperidines to N-protected 1-methoxypiperidines and for the conversion of 1-methoxy-2,3-didehydropiperidine derivatives to 1,2,3-triacetoxypiperidine derivatives. The method provided a new synthetic route to 2S,3S,6-triacetoxy-5S-methylpiperidine and 2R,3R,6-triacetoxy-5S-methylpiperidine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.036
• 作为产物：
  描述：

  N-methoxycarbonyl-2-methoxy-6S-methoxycarbonylpiperidine 在 platinum(IV) oxide 氢气 、 氯化铵 作用下， 以 甲醇 为溶剂， 生成 (S,S)-piperidinedicarboxylic acid dimethyl ester
  参考文献：
  名称：

  阳极氧化将无环α，ω-二氨基酸转化为环状不饱和α-氨基酸的新方法

  摘要：

  非环α，ω二氨基羧酸，大号鸟氨酸和大号赖氨酸，转化到光学纯环状α'，β使用阳极氧化的关键步骤“不饱和α氨基酸。

  DOI：

  10.1039/c39830001169

文献信息

• New synthetic method of optically active α-methylproline and α-methyl-pipecolinic acid using electrochemical oxidation as a key reaction
  作者：Yoshihiro Matsumura、Toshio Kinoshita、Yuka Yanagihara、Noriko Kanemoto、Mitsuaki Watanabe

  DOI：10.1016/0040-4039(96)01919-3

  日期：1996.11

  method consisted of electrochemical α′-methoxylation of the α-amino acid derivatives, the replacement of the α′-methoxy group with a phenylthio group, α-methylation, and reductive removal of the α′-phenylthio group, successively. The intermediates in this method could be used for the preparation of optically active acyclic α-methylated α-amino acids.

  提出了一种新的方法，用于N-保护的L-脯氨酸和L-哌啉酸酯的立体选择性α-甲基化。该方法包括依次进行α-氨基酸衍生物的电化学α'-甲氧基化，用苯硫基取代α'-甲氧基，α-甲基化和还原性除去α'-苯硫基。该方法中的中间体可用于制备光学活性的无环α-甲基化的α-氨基酸。
• A new method for regioselective synthesis of 2-substituted 1-(methoxycarbonyl)-1,2-dihydropyridines
  作者：Tatsuya Shono、Yoshihiro Matsumura、Osamu Onomura、Yasufu Yamada

  DOI：10.1016/s0040-4039(01)83864-8

  日期：1987.1

  2-Substituted 1,2-dihydropyridines including an optically active one were regioselectively prepared from 2-substituted piperidines through three intermediates, that is, (a) 1,2,3,4-tetrahydropyridines, (b) 5-bromo-6-methoxypiperidines, and (c) 1,2,3,6-tetrahydro- 6-methoxypyridines.

  由2-取代的哌啶通过三种中间体，即（a）1,2,3,4-四氢吡啶，（b）5-溴-6-，区域选择性地制备包括光学活性的2-取代的1,2-二氢吡啶。甲氧基哌啶，和（c）1,2,3,6-四氢-6-甲氧基吡啶。
• Enantioselective Synthesis of <i>cis</i> and <i>trans</i> 4-Aminopipecolic Acids as γ-Amino Acids for the Construction of Cyclic RGD-Containing Peptidomimetics Antagonists of α_V β₃ Integrin
  作者：Francesca Dordoni、Dina Scarpi、Francesca Bianchini、Alessandro Contini、Ernesto G. Occhiato

  DOI：10.1002/ejoc.202000634

  日期：2020.8.2

  A stereodivergent preparation of cis and trans 4‐aminopipecolic acids (4‐APAs) was developed from a common precursor to obtain suitably protected, constrained γ‐amino acids useful in peptidomimetic synthesis. Two antagonists of αVβ3 integrin were synthesized.

  从常见的前体中开发出了顺式和反式4-氨基哌酸（4-APA）的立体发散剂，以获得可适当保护，受约束的γ-氨基酸，可用于拟肽合成。α的两个拮抗剂V β 3整联合成。
• Stereoselective synthesis of 3-deoxy-piperidine iminosugars from l-lysine
  作者：Noriaki Moriyama、Yoshihiro Matsumura、Masami Kuriyama、Osamu Onomura

  DOI：10.1016/j.tetasy.2009.11.028

  日期：2009.12

  A new method using electrochemical oxidation and/or OsO4 oxidation has been used for the stereoselective synthesis of 2,3,6-trihydroxylated (5S)-piperidine derivatives. The electrochemical method was successively used for the conversion of N-protected piperidines to N-protected 1-methoxpiperidines and for the conversion of 2,3-didehydro-1-methoxypiperidine derivatives to 2,3-trans-1,2,3-triacetoxypiperidine derivatives. These triacetates were easily transformed into (2S,3S)-6-triacetoxy-(5S)-methylpiperidine and (2R,3R)-6-triacetoxy-(5S)-methylpiperidine. In addition, the 2,3-cis-dihydroxylation of 2,3-didehydro-1-methoxypiperidine derivatives with OsO4 afforded (2R,3S)-6-triacetoxy-(5S)-methylpiperidine and (2S,3R)-(3-triacetoxy-(5S)-methylpiperidine. (C) 2009 Elsevier Ltd. All rights reserved.
• Electroorganic chemistry. 100. A new stereoselective method of synthesis of pyrrolizidines and indolizidines
  作者：Tatsuya Shono、Naoki Kise、Takayoshi Tanabe

  DOI：10.1021/jo00242a004

  日期：1988.4