tert-butyl (3aR,4R,6aR)-4-({[(tert-butyl)dimethylsilyl]oxy}methyl)-2,2-dimethyl-6-oxotetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate | 178456-80-9

• 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 (3aR,4R,6aR)-4-({[(tert-butyl)dimethylsilyl]oxy}methyl)-2,2-dimethyl-6-oxotetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• 英文别名: N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-4-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactam；tert-butyl (3aR,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-4-oxo-6,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 178456-80-9
• 化学式: C₁₉H₃₅NO₆Si
• 分子量: 401.576
• InChiKey: KADRSKVHGJRTKT-MGPQQGTHSA-N

物化性质

• 沸点：
  474.6±45.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (3aR,4R,6aR)-4-({[(tert-butyl)dimethylsilyl]oxy}methyl)-2,2-dimethyl-6-oxotetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 在 四氢呋喃 、 盐酸 、 三乙基硅烷 、 ruthenium(IV) oxide 、 sodium periodate 、 三氟化硼乙醚 、 四丁基氟化铵 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 8.58h， 生成 (2S,3R,4S)-3,4-二羟基吡咯烷-2-羧酸
  参考文献：
  名称：

  Total synthesis of both enantiomers of trans-2,3-cis-3,4-dihydroxyproline

  摘要：

  Both enantiomers of trans-2,3-cis-3,4-dihydroxyproline, 4 and 5, have been stereoselectively synthesized from 2,3-O-isopropylidene-D-glyceraldehyde 1, by taking advantage of a divergent and parallel synthetic strategy, utilizing N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as the common four-carbon synthon. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00123-1
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole 在 咪唑 、 2,6-二甲基吡啶 、 二环己烷并-18-冠醚-6 、 potassium permanganate 、 sodium periodate 、 三氟化硼乙醚 、 silica gel 、 对甲苯磺酸 、 柠檬酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 35.33h， 生成 tert-butyl (3aR,4R,6aR)-4-({[(tert-butyl)dimethylsilyl]oxy}methyl)-2,2-dimethyl-6-oxotetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
  参考文献：
  名称：

  Total synthesis of both enantiomers of trans-2,3-cis-3,4-dihydroxyproline

  摘要：

  Both enantiomers of trans-2,3-cis-3,4-dihydroxyproline, 4 and 5, have been stereoselectively synthesized from 2,3-O-isopropylidene-D-glyceraldehyde 1, by taking advantage of a divergent and parallel synthetic strategy, utilizing N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as the common four-carbon synthon. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00123-1

文献信息

• Stereoselective synthesis of C-4′-aminouridines (uracil C-4-amino-D-ribonucleosides)
  作者：Masataka Yokoyama、Taku Ikenogami、Hideo Togo

  DOI：10.1039/b002063j

  日期：——

  The first C-4′-aminouridines can be synthesized in an α,β-stereoselective manner starting from L-glutamic acid. For the synthesis of α-C-4′-aminouridine, a key compound 9 is cyclized with trifluoroacetic acid followed by reduction with NaBH3CN, while 9 is reduced with NaBH4 followed by mesylation to give β-C-4′-aminouridine. Further, an acetonide-protection method is preferred for the synthesis of α-C-4′-aminouridine.

  第一种C-4′-氨基尿苷可以从L-谷氨酸以α,β-立体选择性的方式合成。对于α-C-4′-氨基尿苷的合成，关键化合物9与三氟乙酸环化，然后用NaBH3CN还原，而9则用NaBH4还原后进行美克化反应，得到β-C-4′-氨基尿苷。此外，在合成α-C-4′-氨基尿苷时，更倾向于使用醋酮保护方法。
• 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.
• Inhibition of LuxS by S-ribosylhomocysteine analogues containing a [4-aza]ribose ring
  作者：Venkata L.A. Malladi、Adam J. Sobczak、Tiffany M. Meyer、Dehua Pei、Stanislaw F. Wnuk

  DOI：10.1016/j.bmc.2011.07.043

  日期：2011.9

  LuxS (S-ribosylhomocysteinase) catalyzes the cleavage of the thioether linkage of S-ribosylhomocysteine (SRH) to produce homocysteine and 4,5-dihydroxy-2,3-pentanedione (DPD), the precursor to a small signaling molecule that mediates interspecies bacterial communication called autoinducer 2 (AI-2). Inhibitors of LuxS should interfere with bacterial interspecies communication and potentially provide a novel class of antibacterial agents. In this work, SRH analogues containing substitution of a nitrogen atom for the endocyclic oxygen as well as various deoxyriboses were synthesized and evaluated for LuxS inhibition. Two of the [4-aza] SRH analogues showed modest competitive inhibition (K-I similar to 40 mu M), while most of the others were inactive. One compound that contains a hemiaminal moiety exhibited time-dependent inhibition, consistent with enzyme-catalyzed ring opening and conversion into a more potent species (K-I* = 3.5 mu M). The structure-activity relationship of the designed inhibitors highlights the importance of both the homocysteine and ribose moieties for high-affinity binding to LuxS active site. (C) 2011 Elsevier Ltd. All rights reserved.