(3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)-1-methylpyrrolidine-2,5-dione | 133710-11-9

• 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: (3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)-1-methylpyrrolidine-2,5-dione
• 英文别名: (3R,4R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-1-methylpyrrolidine-2,5-dione
• CAS: 133710-11-9
• 化学式: C₁₇H₃₅NO₄Si₂
• 分子量: 373.64
• InChiKey: XZOPQYQTPYVDGC-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)-1-methylpyrrolidine-2,5-dione 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3R,4S,5S)-5-Benzyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pyrrolidin-2-one
  参考文献：
  名称：

  使用具有C 2对称性的环状酰亚胺的手性烷基化内酰胺的新型合成策略

  摘要：

  在路易斯酸存在下，用Et 3 SiH容易地由C 2对称酰亚胺的烷基化反应制得的季铵α-羟基内酰胺的还原脱氧显示出极高的立体选择性以提供相应的内酰胺。通过空前的反式反应，通过转化成已知的内酰胺，已明确确认生成的新的立体异构中心的立体化学是S。

  DOI：

  10.1016/s0957-4166(00)80339-0
• 作为产物：
  描述：

  (3R,4R)-3,4-diacetoxy-1-methylpyrrolidine-2,5-dione 在 咪唑 、 乙酰氯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)-1-methylpyrrolidine-2,5-dione
  参考文献：
  名称：

  Dicaffeoyl- or digalloyl pyrrolidine and furan derivatives as HIV integrase inhibitors

  摘要：

  Human immunodeficiency virus (HIV) integrase (IN) catalyzes the integration of HIV DNA copy into the host cell DNA. Such integration is essential for the production of progeny viruses, and therefore therapeutic agents that can inhibit this process should be effective anti-HIV agents. We have previously reported the inhibitory activity of dicaffeoylglucosides against HIV IN. In the present study, we have synthesized and tested dicaffeoyl or digalloyl compounds joined through a five-membered heterocyclic ring as HIV IN inhibitors to explore the SARs of this family of compounds. The starting heterocyclic diols were prepared from L-tartaric acid, diethyl L-tartarate or D-(+)-ribonic gamma -lactone. We found that the HIV IN inhibitory activities of dicaffeoyl derivatives were comparable to that of L-chicoric acid (IC50 = 24.9 muM). On the other hand, digalloyl derivatives were more potent than L-chicoric acid with IC50 Values of 4.7-15.6 muM. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00013-x

文献信息

• Chiral cyclic imides with c2-symmetry. Novel reagents for the synthesis of optically pure lactones containing three contiguous tertiary centers
  作者：Hidemi Yoda、Koji Shirakawa、Kunihiko Takabe

  DOI：10.1016/s0040-4039(00)92719-9

  日期：1991.7

  Asymmetric reactions employing C2-symmetrical imides readily prepared from L-tartaric acid with Grignard reagents and sodium borohydride afforded a separable mixture of two hydroxyamides with high diastereoselectivity. Products were lactonized respectively to provide optically pure γ- alkylated lactones with contiguous tertiary carbon centers. The reaction mechanisms in asymmetric induction were also

  使用由L-酒石酸与Grignard试剂和氢硼化钠轻松制备的C 2-对称酰亚胺进行的不对称反应提供了具有高非对映选择性的两种羟酰胺的可分离混合物。将产物分别内酯化以提供具有连续的叔碳中心的光学纯的γ-烷基化内酯。还讨论了不对称诱导中的反应机理。
• Diastereomer differentiation during 1,2-addition of Grignard reagents under rotamer distribution control
  作者：Hidemi Yoda、Hidekazu Kitayama、Kunihiko Takabe、Akikazu Kakehi

  DOI：10.1016/s0957-4166(00)80410-3

  日期：1993.8

  Construction of (R)-tertiary alcohols through diastereofacial differentiation under rotamer distribution control was accomplished with complete selectivity by means of simple nucleophilic addition of Grignard reagents to chiral α-ketoamides elaborated from C2-symmetrical imides and the absolute configuration was established by an X-ray crystallographic analysis.

  在旋转异构体分布控制下，通过非对面分化构建（R）叔醇，是通过将格氏试剂简单亲核加到C 2对称酰亚胺制得的手性α-酮酰胺上而完全选择性地完成的，并且绝对构型由X确定射线晶体学分析。
• Yoda, Hidemi; Shirakawa, Koji; Takabe, Kunihiko, Chemistry Letters, 1991, # 3, p. 489 - 490
  作者：Yoda, Hidemi、Shirakawa, Koji、Takabe, Kunihiko

  DOI：——

  日期：——
• YODA, HIDEMI;SHIRAKAWA, KOJI;TAKABE, KUNIHIKO, CHEM. LETT.,(1991) N, C. 489-490
  作者：YODA, HIDEMI、SHIRAKAWA, KOJI、TAKABE, KUNIHIKO

  DOI：——

  日期：——
• Dicaffeoyl- or digalloyl pyrrolidine and furan derivatives as HIV integrase inhibitors
  作者：Dong Jin Hwang、Sun Nam Kim、Jung Hoon Choi、Yong Sup Lee

  DOI：10.1016/s0968-0896(01)00013-x

  日期：2001.6

  Human immunodeficiency virus (HIV) integrase (IN) catalyzes the integration of HIV DNA copy into the host cell DNA. Such integration is essential for the production of progeny viruses, and therefore therapeutic agents that can inhibit this process should be effective anti-HIV agents. We have previously reported the inhibitory activity of dicaffeoylglucosides against HIV IN. In the present study, we have synthesized and tested dicaffeoyl or digalloyl compounds joined through a five-membered heterocyclic ring as HIV IN inhibitors to explore the SARs of this family of compounds. The starting heterocyclic diols were prepared from L-tartaric acid, diethyl L-tartarate or D-(+)-ribonic gamma -lactone. We found that the HIV IN inhibitory activities of dicaffeoyl derivatives were comparable to that of L-chicoric acid (IC50 = 24.9 muM). On the other hand, digalloyl derivatives were more potent than L-chicoric acid with IC50 Values of 4.7-15.6 muM. (C) 2001 Elsevier Science Ltd. All rights reserved.