N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester | 16257-73-1

• 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: N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester
• 英文别名: 1-(Toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carboxylic acid methyl ester；methyl (2S,4R)-1-(4-methylphenyl)sulfonyl-4-(4-methylphenyl)sulfonyloxypyrrolidine-2-carboxylate
• CAS: 16257-73-1
• 化学式: C₂₀H₂₃NO₇S₂
• 分子量: 453.537
• InChiKey: ICILFGNGVHEIRZ-APWZRJJASA-N

物化性质

• 熔点：
  85-86 °C
• 沸点：
  604.9±65.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester 在 palladium on activated charcoal sodium azide 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 methyl (2S,4S)-4-amino-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Trans-4-aminoproline, a phytotoxic metabolite with herbicidal activity produced by Ascochyta caulina

  摘要：

  A phytotoxic metabolite, characterized through NMR techniques and synthetic methods as trans-4-aminoproline, was isolated from the culture filtrates of Ascochyta caulina, a promising mycoherbicide for biological control of Chenopodium album. The metabolite, which shows interesting phytotoxic properties, together with ascaulitoxin (recently characterized as N-2-beta-D-glucoside of the unusual bis-amino acid 2,4,7-triamino-5-hydroxyoctandioc acid) and another unidentified compound, compose an active fraction of A. caulina culture filtrates with promising herbicidal properties. When assayed on leaves of host and non host dicots, including wild and cultivated plants, the trans-4-aminoproline showed a wide range of toxicity, with leaves of C. album being the most sensitive. Other interesting aspects were its inefficacy on several monocots, both cultivated and wild and its lack of antifungal, antibiotic and zootoxic activities. This is the first report on trans-4-aminoproline as naturally occurring compound and phytotoxic metabolite produced by A. caulina. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00507-5
• 作为产物：
  描述：

  N-tosyl-trans-4-hydroxy-L-proline 在 吡啶 、 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 171.0h， 生成 N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester
  参考文献：
  名称：

  由（2S）-3,4-脱氢脯氨酸衍生物合成（2R，3R，4S）-2-羟甲基吡咯烷-3,4-二醇。

  摘要：

  由N-保护的（2S）-3,4经五步合成（2R，3R，4S）-2-羟甲基吡咯烷-3,4-二醇（1,4-二脱氧-1,4-亚氨基-D-核糖醇） -脱氢脯氨酸甲酯。四氧化与脱氢脯氨酸衍生物的立体选择反应得到高产率的（2S，3R，4S）-3,4-二羟基脯氨酸（2,3-trans-3,4-cis-3,4-二羟基-L-脯氨酸）伴随少量（<15％）的非对映异构体（2S，3S，4R）-3,4-二羟基脯氨酸（2,3-cis-3,4-cis-3,4-二羟基-L-脯氨酸）。将非对映异构二醇的混合物转化为异亚丙基乙缩醛，并且异构体在制备规模上有效分离。将得到的受保护的（2S，3R，4S）-3,4-二羟基脯氨酸甲酯还原（LiBH4）成2-羟基甲基吡咯烷并脱保护，从而产生（2R，3R，4S）-2-羟基甲基吡咯烷-3，高产高纯度的4-二醇。产品的1H和13C NMR信号已使用二维NMR技术进行了明确分配，并且标题吡咯烷的

  DOI：

  10.1016/0008-6215(94)84059-8

文献信息

• Synthesis of (2R,3R,4S)-2-hydroxymethylpyrrolidine-3,4-diol from (2S)-3,4-dehydroproline derivatives
  作者：Deepa M. Goli、Bruce V. Cheesman、Mohamed E. Hassan、Rita Lodaya、James T. Slama

  DOI：10.1016/0008-6215(94)84059-8

  日期：1994.6

  (2R,3R,4S)-2-Hydroxymethylpyrrolidine-3,4-diol (1,4-dideoxy-1,4-imino-D-ribitol) was synthesized in five steps from N-protected (2S)-3,4-dehydroproline methyl esters. The stereoselective reaction of osmium tetraoxide with dehydroproline derivatives gave high yields of (2S,3R,4S)-3,4-dihydroxyprolines (2,3-trans-3,4-cis-3,4-dihydroxy-L-prolines) accompanied by small amounts (< 15%) of the diastereomeric

  由N-保护的（2S）-3,4经五步合成（2R，3R，4S）-2-羟甲基吡咯烷-3,4-二醇（1,4-二脱氧-1,4-亚氨基-D-核糖醇） -脱氢脯氨酸甲酯。四氧化与脱氢脯氨酸衍生物的立体选择反应得到高产率的（2S，3R，4S）-3,4-二羟基脯氨酸（2,3-trans-3,4-cis-3,4-二羟基-L-脯氨酸）伴随少量（<15％）的非对映异构体（2S，3S，4R）-3,4-二羟基脯氨酸（2,3-cis-3,4-cis-3,4-二羟基-L-脯氨酸）。将非对映异构二醇的混合物转化为异亚丙基乙缩醛，并且异构体在制备规模上有效分离。将得到的受保护的（2S，3R，4S）-3,4-二羟基脯氨酸甲酯还原（LiBH4）成2-羟基甲基吡咯烷并脱保护，从而产生（2R，3R，4S）-2-羟基甲基吡咯烷-3，高产高纯度的4-二醇。产品的1H和13C NMR信号已使用二维NMR技术进行了明确分配，并且标题吡咯烷的
• Enantioselective Synthesis of Quaternary Oxindoles: Desymmetrizing Staudinger–Aza-Wittig Reaction Enabled by a Bespoke HypPhos Oxide Catalyst
  作者：Changmin Xie、Jacob Kim、Binh Khanh Mai、Shixuan Cao、Rong Ye、Xin-Yi Wang、Peng Liu、Ohyun Kwon

  DOI：10.1021/jacs.2c09421

  日期：2022.11.23

  asymmetric Staudinger–aza-Wittig reaction of (o-azidoaryl)malonates, allowing access to chiral quaternary oxindoles through phosphine oxide catalysis. We designed a novel HypPhos oxide catalyst to enable the desymmetrizing Staudinger–aza-Wittig reaction through the PIII/PV═O redox cycle in the presence of a silane reductant and an IrI-based Lewis acid. The reaction occurs under mild conditions, with

  本文描述了(邻叠氮基芳基)丙二酸酯的催化不对称施陶丁格-氮杂-维蒂希反应，允许通过氧化膦催化获得手性季羟吲哚。我们设计了一种新型 HypPhos 氧化物催化剂，可在硅烷还原剂和 Ir I基路易斯酸存在下通过 P III /P V =O 氧化还原循环实现去对称 Staudinger-aza-Wittig 反应。该反应条件温和，官能团耐受性好，底物范围广，具有优异的对映选择性。密度泛函理论表明，去对称反应中的对映选择性源于 Ir I物种和 HypPhos 催化剂的协同作用。该方法的实用性通过七种生物碱靶标的（正式）合成得到证明：(−)-胶粘蛋白 C、(−)-coerulescine、(−)-horsfiline、(+)-deoxyeseroline、(+)-esermethole、( +)-毒扁豆碱和(+)-毒扁豆碱。
• Synthesis of new sulfonyl pyrrolidine derivatives as matrix metalloproteinase inhibitors
  作者：Xian-Chao Cheng、Qiang Wang、Hao Fang、Wei Tang、Wen-Fang Xu

  DOI：10.1016/j.bmc.2008.07.073

  日期：2008.9

  A series of new sulfonyl pyrrolidine derivatives was designed, synthesized, and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and aminopeptidase N (AP-N). The results showed that these pyrrolidine derivatives exhibited highly selective inhibition against MMP-2 as compared with AP-N. The compounds 4c, 4j, 5a, and 5b were equally or more potent MMP-2 inhibitors than the positive control LY52. The FlexX docking was done to explain the reason for the different potency between MMP-2 and AP-N. Structure-activity relationships were also briefly discussed. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and biological properties of a new series of 5-substituted-pyrimidine-L-nucleoside analogues
  作者：Nigel B. Westwood、Richard T. Walker

  DOI：10.1016/s0040-4020(98)00821-7

  日期：1998.10

  trans-4-hydroxy-L-proline (5) has been elaborated into a new series of pyrrolidine-L-nucleoside analogues incorporating non-standard 5-substituted-pyrimidine nucleobases, via the azidopyrrolidines 12 and 13. Those analogues employing an acyl protecting group on the primary hydroxyl functionality underwent radical bromination of the ethyl side chain of the pyrimidine ring, to provide E-5-(2-bromovinyl)uracil-pyrrolidine-L-nucleosides 23-26. Of the compounds assessed for potential antiviral activity only 5-ethyluracil-(benzoyloxymethyl)pyrrolidine 20 was found to be a specific inhibitor of vaccinia virus. (C) 1998 Elsevier Science Ltd. All rights reserved.
• KRAPCHO, J.;WADE, P. C.
  作者：KRAPCHO, J.、WADE, P. C.

  DOI：——

  日期：——