(2S,5R)-N-benzyl-5-methoxycarbonylproline | 102572-59-8

• 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: (2S,5R)-N-benzyl-5-methoxycarbonylproline
• 英文别名: (2S,5R)-1-Benzyl-5-(methoxycarbonyl)pyrrolidine-2-carboxylic acid；(2S,5R)-1-benzyl-5-methoxycarbonylpyrrolidine-2-carboxylic acid
• CAS: 102572-59-8
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: PPRLCASKVDQSEK-NWDGAFQWSA-N

物化性质

• 沸点：
  397.9±42.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,5R)-N-benzyl-5-methoxycarbonylproline 在 咪唑 、 aluminum oxide 、 sodium tetrahydroborate 、 草酰氯 、 偶氮二异丁腈 、 三正丁基氢锡 、 氯甲酸乙酯 、 sodium hydride 、 二异丁基氢化铝 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 105.16h， 生成 ((2R,5S)-1-Benzyl-5-hydroxymethyl-pyrrolidin-2-ylmethyl)-phosphonic acid dimethyl ester
  参考文献：
  名称：

  Catalytic Antibodies in Synthesis:  Design and Synthesis of a Hapten for Application to the Preparation of a Scalemic Pyrrolidine Ring Synthon for Ptilomycalin A

  摘要：

  A catalytic antibody-based approach toward the synthesis of an optically active pyrrolidine ring synthon potentially useful for ptilomycalin A is described. Enantiomerically pure hapten 37 was designed and constructed with the eventual goal of generating antibodies for the enantioselective partial hydrolysis of a meso diester such as 44 into a monoacid 45. This transition state analog possesses a phosphonate group containing the requisite oxyanionic character of the tetrahedral intermediate for ester hydrolysis. A newly developed carbamate-based linker, which was found to be much more hydrolytically stable than the commonly used glutarate ester, was developed for coupling of the hapten to a carrier protein.

  DOI：

  10.1021/jo951469t
• 作为产物：
  描述：

  己二酰氯 在 pig liver esterase 、 溴 、 caesium carbonate 作用下， 以 aq. phosphate buffer 、 乙酸乙酯 、 丙酮 为溶剂， 反应 35.0h， 生成 (2S,5R)-N-benzyl-5-methoxycarbonylproline
  参考文献：
  名称：

  A mechanochemical approach to access the proline–proline diketopiperazine framework

  摘要：

  球磨法被利用来通过机械化学亲核取代制备一个取代的脯氨酸构建块。随后，发展了受阻脯氨酸衍生物的机械偶联，以在无溶剂条件下提供脯氨酸-脯氨酸二肽。去保护-环化序列产生了相应的二酮哌嗪，其高立体选择性可以通过DFT计算来解释。使用这种方法，一个对映纯的二取代脯氨酸-脯氨酸二酮哌嗪在4个步骤中合成，利用了球磨机制造了5个新键。

  DOI：

  10.3762/bjoc.13.217

文献信息

• Enzymatic desymmetrization of pyrrolidine and pyrroline derivatives
  作者：Robert Chênevert、Frédéric Jacques、Pascall Giguère、Mohammed Dasser

  DOI：10.1016/j.tetasy.2008.05.022

  日期：2008.6

  The enzymatic desymmetrization of various meso-N-Boc-2,5-cis-disubstituted pyrrolidines and pyrrolines compounds by ester hydrolysis or transesterification provided the corresponding monoesters in high enantiomeric excess.

  各种的酶desymmetrization内消旋- ñ -Boc-2,5-顺式二取代的吡咯烷和吡咯啉化合物通过酯水解或酯交换提供高对映体过量的相应单酯。
• Highly enantioselective route to (R)-proline derivatives via enzyme catalysed hydrolysis of cis-N-benzyl-2,5-bismethoxycarbonylpyrrolidine in an aqueous dimethyl sulphoxide medium
  作者：Fredrik Björkling、John Boutelje、Mats Hjalmarsson、Karl Hult、Torbjörn Norin

  DOI：10.1039/c39870001041

  日期：——

  Pig liver esterase catalysed hydrolysis of diester (1) with dimethyl sulphoxide as cosolvent in buffered solutions gave optically pure monoester (2) which was further transformed to the (R)-proline related ester (4) by radical decarboxylation.

  猪肝酯酶在缓冲溶液中用二甲亚砜作为助溶剂催化二酯（1）水解，得到光学纯的单酯（2），其通过自由基脱羧作用进一步转化为（R）-脯氨酸相关的酯（4）。
• INTERMEDIATE FOR SYNTHESIS OF CARBAPENEM AND PRODUCTION OF SAID INTERMEDIATE
  申请人：Ajinomoto Co., Inc.

  公开号：EP0513398A1

  公开（公告）日：1992-11-19

  A carbapenem derivative having an R-configuration at the 5-position, represented by general formula (I), and optically active pyrrolidine derivatives represented by general formulae (XI) and (XII), all of these compounds serving as the intermediate for the synthesis of carbapenems as β-lactam antibiotics. In formula (I) R¹ represents hydrogen or an organic group; and R² represents hydrogen or a carboxyl protective group. In formulae (XI) and (XII) R¹ represents benzyl; R² represents alkyl; R³ represents alkyl, benzyl or allyl; R⁴ represents hydrogen, alkyl, vinyl, phenyl, benzyl or a heterocyclic group containing 1 to 4 nitrogen or/and oxygen atoms; and R⁵ represents hydrogen or methyl.

  通式(I)表示的具有 5 位 R 构型的碳青霉烯类衍生物，以及通式(XI)和(XII)表示的具有光学活性的吡咯烷衍生物，所有这些化合物均可作为合成碳青霉烯类β-内酰胺抗生素的中间体。在式 (I) 中，R¹ 代表氢或有机基团；R² 代表氢或羧基保护基团。在式(XI)和(XII)中，R¹代表苄基；R²代表烷基；R³代表烷基、苄基或烯丙基；R⁴代表氢、烷基、乙烯基、苯基、苄基或含有 1 至 4 个氮原子或/和氧原子的杂环基团；R⁵代表氢或甲基。
• Diversified synthetic approaches to the carbapenem antibiotics based on symmetrization-asymmetrization concept
  作者：Masa-aki Kurihara、Keiji Kamiyama、Susumu Kobayashi、Masaji Ohno

  DOI：10.1016/s0040-4039(00)98938-x

  日期：——
• Méthyl<i>N</i>-[(2<i>R</i>,5<i>S</i>)-1-<i>N</i>-Benzyl-5-méthoxycarbonylprolyl]-(<i>S</i>)-phénylalaninate
  作者：A. Chiaroni、C. Riche、T. Zair、F. Guenoun、R. Lazaro、P. Viallefont

  DOI：10.1107/s0108270196014606

  日期：1997.4.15

  In order to prepare new chiral auxiliaries useful in developing a new method of synthesis of optically pure amines or beta-amino acids, an unsymmetric derivative of pyrrolidine has been obtained, methyl 2-[(2R,5S)-(1-benzyl-5-methoxypyrrolidin-2-yl)carbonyl-(S)-amino]-3-phenylpropanoate, C24H28N2O5. This has been crystallized and subjected to X-ray analysis in order to ascertain the absolute configuration of the two asymmetric C atoms of the ring, The five-membered ring is half-chair shaped. An intramolecular hydrogen bond links the amino N atom of the phenylalanine group to the carbonyl of the 5-methoxycarbonyl group.