(2S,4S)-1,2-二苄氧羰基-4-羟基吡咯烷 | 132592-07-5

• 物质功能分类: 有机原料 - 杂环化合物
• 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
• 中文名称: (2S,4S)-1,2-二苄氧羰基-4-羟基吡咯烷
• 中文别名: (2S,4S)-4-羟基-1,2-吡咯烷二羧酸1,2-双(苯基甲基)酯
• 英文名称: (2S,4S)-4-hydroxy-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester)
• 英文别名: N^α-benzyloxycarbonyl-cis-4-hydroxy-L-proline benzyl ester；(2S,4S)-dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate；dibenzyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate
• CAS: 132592-07-5
• 化学式: C₂₀H₂₁NO₅
• 分子量: 355.39
• InChiKey: XHKMBFDLCAZWCR-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  (2S,4S)-1,2-二苄氧羰基-4-羟基吡咯烷 在 4-二甲氨基吡啶 、 四乙基对甲苯磺酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2S,4S,5RS)-5-methoxy-4-(pivaloyloxy)-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester)
  参考文献：
  名称：

  Electrochemical oxidation of proline derivatives: total syntheses of bulgecinine and bulgecin C

  摘要：

  The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented. Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsily)ethyl) ester (19). The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent. Bulgecin C (1c) was prepared via a beta-stereoselective glycosidation reaction using a 2-azido-2-deoxy-alpha-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.

  DOI：

  10.1021/jo00008a040
• 作为产物：
  描述：

  (2s,4r)-1,2-二苄氧羰基-4-羟基吡咯烷 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 (2S,4S)-1,2-二苄氧羰基-4-羟基吡咯烷
  参考文献：
  名称：

  Syntheses of de(hydroxymethyl)desulfo analogues of bulgecins A, B and C

  摘要：

  The syntheses of de(hydroxymethyl)desulfo analogues of bulgecin A, B and C are described. Stereospecific beta-glycosylation of aglycones was achieved using Schmidt's trichloroacetimidate methodology.

  DOI：

  10.1016/0040-4039(94)85078-x

文献信息

• l-Proline-Catalyzed Asymmetric Michael Addition of 2-Oxindoles to Enones: A Convenient Access to Oxindoles with a Quaternary Stereocenter
  作者：Svetlana Tsogoeva、Matthias Freund

  DOI：10.1055/s-0030-1259527

  日期：2011.3

  A new organocatalytic approach for 1,4-conjugate addition of 2-oxindoles to α,β-unsaturated ketones using the combination of readily available and nonexpensive l-proline and achiral trans-2,5-dimethylpiperazine as catalytic system is provided. The reaction results in oxindole derivatives with vicinal quaternary and tertiary carbon centers in up to 99% yield and 91% ee.

  提供了一种新的有机催化方法，用于将2-氧吲哚与α,β-不饱和酮进行1,4-加成，采用廉价且易得的l-脯氨酸和非手性的反式-2,5-二甲基哌嗪作为催化体系。反应产生的吲哚衍生物具有相邻的季碳和三级碳中心，产率高达99%，对映体过量达到91%。
• Advances towards Highly Active and Stereoselective Simple and Cheap Proline-Based Organocatalysts
  作者：Francesco Giacalone、Michelangelo Gruttadauria、Paola Agrigento、Paolo Lo Meo、Renato Noto

  DOI：10.1002/ejoc.201000913

  日期：2010.10

  at loadings of 2–0.1 mol-% for the direct asymmetric aldol reaction in water by using variable amounts of water. Among them, a new catalyst, the L-proline carrying a trans-4-(2,2-diphenylacetoxy) group, and a catalyst previously synthesized by us, the L-proline carrying a trans-4-(4-phenylbutanoyloxy) group, were found to be excellent catalysts for the aldol reaction between cyclohexanone or cyclopentanone

  通过使用不同量的水，筛选出 10 种 4-酰氧基-L-脯氨酸作为催化剂，负载量为 2-0.1 mol-%，用于在水中的直接不对称羟醛反应。其中，新型催化剂L-脯氨酸带有反式4-(2,2-二苯基乙酰氧基)基团，以及我们之前合成的催化剂L-脯氨酸带有反式4-(4-苯基丁酰氧基)基团, 被发现是环己酮或环戊酮与取代苯甲醛之间羟醛反应的优良催化剂，当分别以 1 和 0.5 mol-% 在室温下使用时，没有添加剂。对于此类催化剂，获得了高转化率，这是烯胺有机催化获得的最高值之​​一。最后，这些催化剂可以通过廉价分子的直接 O-酰化合成，并成功用于放大反应。
• Novel µ opioid antagonists derived from the µ opioid agonists endomorphin and [Dmt ¹ ]DALDA (H‐Dmt‐D‐Arg‐Phe‐Lys‐NH ₂ )
  作者：Saijian Shi、Jian Xu、LingLing Feng、Xin Fan、Zhen Chen、Yajuan Qin、Nga N. Chung、Tingyou Li、Peter W. Schiller

  DOI：10.1111/cbdd.13743

  日期：2020.11

  Hybrid analogues of the µ opioid agonists endomorphin and [Dmt1]DALDA (H‐Dmt‐D‐Arg‐Phe‐Lys‐NH2, Dmt = 2′,6′‐dimethyltyrosine) containing cis‐4‐amino‐Pro, trans‐4‐amino‐Pro, cis‐4‐aminoethyl‐Pro or cis‐4‐guanidinylethyl‐Pro in the 2 position of the peptide sequence were synthesized. None of the compounds retained high µ opioid agonist activity and, unexpectedly, substitution of cis‐4‐amino‐Pro resulted

  µ 阿片类激动剂内吗啡肽和 [Dmt 1 ]DALDA（H-Dmt-D-Arg-Phe-Lys-NH 2，Dmt = 2',6'-二甲基酪氨酸）的杂合类似物，含有顺式-4-氨基-Pro，反式合成了肽序列第 2 位的-4-氨基-Pro、顺式-4-氨基乙基-Pro 或顺式-4-胍基乙基-Pro 。没有一种化合物保持高μ阿片类激动剂活性，出人意料的是，顺式-4-氨基-Pro的取代产生了一类新型的强效μ阿片拮抗剂。特别是，化合物 H-Dmt- cis -4-amino-Pro-Trp-Lys-NH 2 (CZ-1) 是一种高度选择性的 µ 阿片拮抗剂，具有 ~1 nM µ 受体结合亲和力。
• [EN] DIMERIC PEPTIDE INHIBITORS OF APOPTOSIS PROTEINS<br/>[FR] INHIBITEURS PEPTIDIQUES DIMÈRES DE PROTÉINES D'APOPTOSE
  申请人：HEPAGENE THERAPEUTICS INC

  公开号：WO2019023275A1

  公开（公告）日：2019-01-31

  The present technology is directed to compounds, compositions, and methods related to treatment of cancers and viral infections mediated by lAPs. In particular the present compounds and compositions may be used to treat lAP-mediated ovarian cancer and hepatitis B infection.

  现有技术涉及到与治疗lAPs介导的癌症和病毒感染有关的化合物、组合物和方法。特别是，现有的化合物和组合物可用于治疗lAP介导的卵巢癌和乙型肝炎感染。
• Protected aminooxyprolines for expedited library synthesis: Application to Tsg101-directed proline–oxime containing peptides
  作者：Fa Liu、Andrew G. Stephen、Robert J. Fisher、Terrence R. Burke

  DOI：10.1016/j.bmcl.2007.12.003

  日期：2008.2

  The stereoselective synthesis of aminooxy-containing proline analogues bearing Fmoc/Boc or Fmoc/Mtt protection that renders them suitable for incorporation into peptides using Fmoc protocols is reported. Acid-catalyzed unmasking at the completion of peptide synthesis yields free aminooxy-functionalities for oxime formation through reaction with libraries of aldehydes. This allows post solid-phase diversification strategies that may facilitate structure-activity relationship studies. Published by Elsevier Ltd.