(2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine | 118329-82-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine
• 英文别名: (3R,5S)-5-(Hydroxymethyl)-1-tosylpyrrolidin-3-yl 4-methylbenzenesulfonate；[(3R,5S)-5-(hydroxymethyl)-1-(4-methylphenyl)sulfonylpyrrolidin-3-yl] 4-methylbenzenesulfonate
• CAS: 118329-82-1
• 化学式: C₁₉H₂₃NO₆S₂
• 分子量: 425.527
• InChiKey: VQRFXOBYURQTDE-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine 在 potassium osmate 吡啶 、 lithium hydroxide 、 sodium hydroxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 次氯酸叔丁酯 、 氨 、 双氧水 、 sodium 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 丙醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 17.5h， 生成 (2S,3S,4R)-3-amino-2-hydroxymethyl-4-hydroxypyrrolidine
  参考文献：
  名称：

  （2 S，3 S，4 R）-3-氨基-2-羟甲基-4-羟基吡咯烷的首次不对称合成

  摘要：

  新型（2 S，3 S，4 R）-3-氨基-2-羟基甲基-4-羟基吡咯烷5已由反式-4-羟基-1-脯氨酸8高效合成。关键步骤涉及链烯7的束缚氨基羟基化，以在形成的产物6和13中区域和立体选择性地引入氨基醇官能团。随后的脱保护步骤提供了靶分子5以及几种不同保护的类似物。

  DOI：

  10.1016/j.tetlet.2005.06.025
• 作为产物：
  描述：

  N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester 在 sodium tetrahydroborate 、 乙醇 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine
  参考文献：
  名称：

  四元羟吲哚的对映选择性合成：通过定制 HypPhos 氧化物催化剂实现 Staudinger-Aza-Wittig 去对称反应

  摘要：

  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。

  DOI：

  10.1021/jacs.2c09421

文献信息

• Asymmetric synthesis of 3-amino-4-hydroxy-2-(hydroxymethyl)pyrrolidines as potential glycosidase inhibitors
  作者：Kim L. Curtis、Emma L. Evinson、Sandeep Handa、Kuldip Singh

  DOI：10.1039/b711994a

  日期：——

  Three diastereoisomers of 3-amino-4-hydroxy-2-(hydroxymethyl)pyrrolidine have been synthesised by a divergent route starting from trans-4-hydroxy-L-proline. Regio- and stereoselective introduction of the 3-amino and 4-hydroxyl functional groups was achieved using either a tethered aminohydroxylation reaction or by employing intra- and intermolecular epoxide-opening strategies. Preliminary biological data indicate that two of these novel amino pyrrolidines are moderate inhibitors of β-galactosidase.

  以反式-4-羟基-L-脯氨酸为起点，通过不同的路线合成了 3-氨基-4-羟基-2-(羟甲基)吡咯烷的三种非对映异构体。通过系链氨基羟化反应或分子内和分子间环氧化物开环策略，实现了 3-氨基和 4-羟基官能团的区域和立体选择性引入。初步生物数据表明，这些新型氨基吡咯烷中的两种是β-半乳糖苷酶的温和抑制剂。
• Chemoenzymatic synthesis and cannabinoid activity of a new diazabicyclic amide of phenylacetylricinoleic acid
  作者：Manuel López-Ortíz、Andrea Herrera-Solís、Axel Luviano-Jardón、Nidia Reyes-Prieto、Ivan Castillo、Ivan Monsalvo、Patricia Demare、Mónica Méndez-Díaz、Ignacio Regla、Oscar Prospéro-García

  DOI：10.1016/j.bmcl.2010.04.074

  日期：2010.6

  Endocannabinoids (eCBs) are endogenous neuromodulators of synaptic transmission. Their dysfunction may cause debilitating disorders of diverse clinical manifestation. For example, drug addiction, lack of sex desire, eating disorders, such as anorexia or bulimia and dyssomnias. eCBs also participate in the regulation of core temperature and pain perception. In this context, it is important to recognize the utility of cannabinoid receptor 1 (CB1R) agonists, natural as Delta(9)-tetrahydrocannabinol (THC) or synthetic as Nabilone as useful drugs to alleviate this kind of patients' suffering. Therefore, we have developed a new drug, (R,Z)-18-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-18-oxooctadec-9-en-7-yl phenylacetate (PhAR-DBH-Me), that appears to bind and activate the CB1R. This diazabicyclic amide was synthesized from phenylacetylricinoleic acid and (1S, 4S)-2,5-diazabicyclo[ 2.2.1] heptane. To test its cannabinergic properties we evaluated its effects on core temperature, pain perception, and the sleep-waking cycle of rats. Results indicate that 20 and 40 mg/kg of PhAR-DBH-Me readily reduced core temperature and increased pain perception threshold. In addition, 20 mg/kg increased REM sleep in otherwise normal rats. All these effects were prevented or attenuated by AM251, a CB1R antagonist. Place preference conditioning studies indicated that this molecule does not produce rewarding effects. These results strongly support that PhAR-DBH-Me possesses cannabinoid activity without the reinforcement effects. (C) 2010 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.