tert-butyl (2R,3R,4R)-2-({[(tert-butyl)dimethylsilyl]oxy}methyl)-3,4-dihydroxy-5-oxopyrrolidine-1-carboxylate | 293297-97-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2R,3R,4R)-2-({[(tert-butyl)dimethylsilyl]oxy}methyl)-3,4-dihydroxy-5-oxopyrrolidine-1-carboxylate
• 英文别名: (3R,4R,5R)-N-tert-butoxycarbonyl-3,4-dihydroxy-5-(tert-butyldimethylsiloxymethyl)pyrrolidin-2-one
• CAS: 293297-97-9
• 化学式: C₁₆H₃₁NO₆Si
• 分子量: 361.511
• InChiKey: TWRQFGIFMAKLGJ-IJLUTSLNSA-N

物化性质

• 熔点：
  74-76 °C
• 沸点：
  445.9±45.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  96.3
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R,3R,4R)-2-({[(tert-butyl)dimethylsilyl]oxy}methyl)-3,4-dihydroxy-5-oxopyrrolidine-1-carboxylate 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Total syntheses of N-boc-protected 3′-deoxy-4′-azathymidine and 4′-azauridine

  摘要：

  Novel modified nucleosides 4, 11, ent-11, and 17, wherein the furanose ring oxygen is replaced by nitrogen, have been synthesized by reacting azasugars 3, 10, ent-10, and 15 with silylated uracil or thymine bases.

  DOI：

  10.1016/s0040-4039(00)76729-3
• 作为产物：
  描述：

  N-(tert-Butoxycarbonyl)-6,7-O-isopropylidene-2,3-dideoxy-D-ribo-hept-2-enono-1,4-lactam 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 二环己烷并-18-冠醚-6 、 sodium tetrahydroborate 、 potassium permanganate 、 sodium periodate 、 苯基氯化硒 、 氢气 、 双氧水 、 sodium acetate 、 silica gel 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (2R,3R,4R)-2-({[(tert-butyl)dimethylsilyl]oxy}methyl)-3,4-dihydroxy-5-oxopyrrolidine-1-carboxylate
  参考文献：
  名称：

  Total syntheses of N-boc-protected 3′-deoxy-4′-azathymidine and 4′-azauridine

  摘要：

  Novel modified nucleosides 4, 11, ent-11, and 17, wherein the furanose ring oxygen is replaced by nitrogen, have been synthesized by reacting azasugars 3, 10, ent-10, and 15 with silylated uracil or thymine bases.

  DOI：

  10.1016/s0040-4039(00)76729-3

文献信息

• Combining prolinamides with 2-pyrrolidinone: Novel organocatalysts for the asymmetric aldol reaction
  作者：Ismini Vlasserou、Maria Sfetsa、Dimitrios-Triantafyllos Gerokonstantis、Christoforos G. Kokotos、Panagiota Moutevelis-Minakakis

  DOI：10.1016/j.tet.2018.03.054

  日期：2018.5

  identified as excellent organocatalysts for the aldol reaction. The combination of prolinamides with derivatives bearing the 2-pyrrolidinone scaffold, deriving from pyroglutamic acid, led to the identification of novel organocatalysts for the intermolecular asymmetric aldol reaction. The new hybrids were tested both in organic and aqueous media. Among the compounds tested, 22 afforded the best results in petroleum

  肽，特别是脯氨酰胺已被确认为醛醇缩合反应的优良有机催化剂。脯氨酰胺与衍生自焦谷氨酸的带有2-吡咯烷酮骨架的衍生物的组合导致鉴定用于分子间不对称醛醇缩合反应的新型有机催化剂。新型杂交种在有机和水性介质中均经过测试。在测试的化合物中，有22种化合物在石油醚中的效果最好，而25种化合物在盐水中的产率和选择性高。然后，利用各种酮和醛，高收率（高达100％），优异的非对映异构体（高达97：3 dr）和对映选择性（高达99％）获得醛醇缩合反应的产物。ee）。
• The use of J-coupling as a sole criterion to assign the total absolute stereochemistry of new pyrrolidinone class synthetic analogs, derived from S -pyroglutamic acid
  作者：Tahsin F. Kellici、Dimitrios Ntountaniotis、Marianna Vanioti、Simona Golic Grdadolnik、Mihael Simcic、Georgios Michas、Panagiota Moutevelis-Minakakis、Thomas Mavromoustakos

  DOI：10.1016/j.molstruc.2016.09.075

  日期：2017.2

  Abstract During the synthesis of new pyrrolidinone analogs possessing biological activity it is intriguing to assign their absolute stereochemistry as it is well known that drug potency is influenced by the stereochemistry. The combination of J-coupling information with theoretical results was used in order to establish their total stereochemistry when the chiral center of the starting material has

  摘要 在具有生物活性的新型吡咯烷酮类似物的合成过程中，分配它们的绝对立体化学是很有趣的，因为众所周知药物效力受立体化学的影响。当起始材料的手性中心已知绝对立体化学时，J-偶联信息与理论结果的组合用于建立它们的总立体化学。J 偶联可用作新合成类似物识别正确立体化学的唯一标准。这种方法非常有用，尤其是在 2D NOESY 光谱无法提供此信息的类似物的情况下。很少给出合成例子来证明这种方法的重要性。
• Synthesis of 3‘-Deoxy-3‘-difluoromethyl Azanucleosides from <i>trans</i>-4-Hydroxy-<scp>l</scp>-proline
  作者：Xiao-Long Qiu、Feng-Ling Qing

  DOI：10.1021/jo050057+

  日期：2005.5.1

  Two strategies were tried to synthesize 3'-deoxy-3'-difluoromethyl azanucleosides. After the failure of the first route, the key intermediate 12 from trans-4-hydroxyproline 7 in 8 steps was stereoselectively prepared. The alcohol 12 was subjected to selective protection, oxidation, and difluoromethylenation to afford the fluorinated compound 18, whose hydrogenation was then systematically investigated. After a series of transformations of protecting groups, the resultant compounds 22 and 23 were oxidized to the desired lactams 24 and 25, which were successfully utilized to synthesize our target molecules, 3'-deoxy-3'-difluoromethyl azanucleosides 33, 34a, 34b, and 35.
• Functionalized pyrrolidine inhibitors of human type II α-mannosidases as anti-cancer agents: Optimizing the fit to the active site
  作者：Hélène Fiaux、Douglas A. Kuntz、Daniela Hoffman、Robert C. Janzer、Sandrine Gerber-Lemaire、David R. Rose、Lucienne Juillerat-Jeanneret

  DOI：10.1016/j.bmc.2008.06.021

  日期：2008.8

  Refining the chemical structure of functionalized pyrrolidine-based inhibitors of Golgi alpha-mannosidase II (GMII) to optimize binding affinity provided a lead molecule that demonstrated nanomolar competitive inhibition of alpha-mannosidases II and an optimal fit in the active site of Drosophila GMII by X-ray crystallography. Esters of this lead compound also inhibited the growth of human glioblastoma and brain-derived endothelial cells more than the growth of non-tumoral human fibroblasts, suggesting their potential for anti-cancer therapy.