Carbamic acid, [(1R,2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-formylpropyl]-, 1,1-dimethylethyl ester | 914799-34-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: Carbamic acid, [(1R,2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-formylpropyl]-, 1,1-dimethylethyl ester
• 英文别名: tert-butyl ((2R,3S)-3-((tert-butyldimethylsilyl)-oxy)-1-oxobutan-2-yl)carbamate
• CAS: 914799-34-1
• 化学式: C₁₅H₃₁NO₄Si
• 分子量: 317.501
• InChiKey: YIBMHJQNWZWDTJ-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Carbamic acid, [(1R,2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-formylpropyl]-, 1,1-dimethylethyl ester 在 palladium on activated charcoal 氢气 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 溶剂黄146 作用下， 以 甲醇 、 乙酸乙酯 、 甲苯 、 苯 为溶剂， 反应 50.5h， 生成 ((2S,3S)-6-Hydroxy-2-methyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthetic Studies ofN‐demethylossamine and Elaboration of its Glycosylation

  摘要：

  An amino-sugar, N -demethylossamine, was efficiently synthesized from D-threonine, two stereogenic centers of which were directly used as those at the C-4 and 5 positions of the target sugar. In addition, the glycosylation study indicated that reaction of the acetate 7 with cyclopentanol under Lewis acid conditions, provided the desired alpha-L-glycoside 9 alpha.

  DOI：

  10.1080/07328300600778793
• 作为产物：
  描述：

  methyl (2R,3S)-2-(tert-butoxycarbonylamino)-3-(tert-butyldimethylsilyloxy)butanoate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以12.1 g的产率得到Carbamic acid, [(1R,2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-formylpropyl]-, 1,1-dimethylethyl ester
  参考文献：
  名称：

  Novel Angular Benzophenazines:  Dual Topoisomerase I and Topoisomerase II Inhibitors as Potential Anticancer Agents

  摘要：

  A series of substituted angular benzophenazines were prepared using a new synthetic route via a novel regiocontrolled condensation of 1,2-naphthoquinones and 2,3-diaminobenzoic acids. The synthesis and biological activity of this new series of substituted 8,9-benzo[a]phenazine carboxamide systems are described. The analogues were evaluated against the H69 parental human small cell lung carcinoma cell line and H69/LX4 resistant cell line which overexpresses P-glycoprotein. Selected analogues were evaluated against the COR-L23-parental human non small cell lung carcinoma cell line and the COR-L23/R resistant cell line which overexpresses multidrug resistance protein. This series of novel angular benzophenazines were potent cytotoxic agents in these cell lines and may be able to circumvent multidrug resistance mechanisms which result in the lack of efficacy of many drugs in cancer chemotherapy. These compounds show dual inhibition of topoisomerase I and topoisomerase II and thus target two key enzymes responsible for the topology of DNA that are active at different points in the cell cycle. The introduction of chirality into the carboxamide side chain of these novel benzophenazine carboxamides has resulted in the discovery of a potent enantiospecific series of cytotoxic agents, exemplified by 4-methoxy-benzo[a]phenazine-11-carboxylic acid (2-(dimethylamino)-1-(R)methyl-ethyl)-amide, XR11576 ((R)-4j"). In vivo activity has been demonstrated for 4-methoxy-benzo[a]phenazine-11-carboxylic acid (2-(dimethylamino)-1-(R)-methyl-ethyl)-amide, XR11576, after intravenous administration to female mice, and this compound has been selected as a development candidate for further evaluation.

  DOI：

  10.1021/jm010329a

文献信息

• Total Synthesis of (+)-Jatrophalactam
  作者：Jianhong Gao、Dongyu Sun、Kuan Yu、Hujun Xie、Hanfeng Ding

  DOI：10.1021/acs.orglett.9b03778

  日期：2019.12.6

  The first asymmetric total synthesis of (+)-jatrophalactam was reported, which unambiguously determined the absolute configuration of the titled natural product. The key features entail a conformationally controlled cyclopropanation, a Meldrum’s acid adduct-engaged macrolactam formation, and a Pd(II)-mediated oxidative cyclization.

  报道了第一个不对称的（+）-邻苯二甲内酰胺的全合成，它清楚地确定了标题天然产物的绝对构型。关键特征包括构象控制的环丙烷化，Meldrum的酸加成物结合的大内酰胺形成以及Pd（II）介导的氧化环化。