methyl (2R,3S)-2-(tert-butoxycarbonylamino)-3-(tert-butyldimethylsilyloxy)butanoate | 914799-28-3

• 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: methyl (2R,3S)-2-(tert-butoxycarbonylamino)-3-(tert-butyldimethylsilyloxy)butanoate
• 英文别名: methyl N-(tert-butoxycarbonyl)-O-(tert-butyldimethylsilyl)-D-threoninate
• CAS: 914799-28-3
• 化学式: C₁₆H₃₃NO₅Si
• 分子量: 347.527
• InChiKey: HMLUSNHTPIFCNR-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-2-(tert-butoxycarbonylamino)-3-(tert-butyldimethylsilyloxy)butanoate 在 锂硼氢 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以99%的产率得到[(1S,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxymethyl-propyl]-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：

  二碳酸二叔丁酯 在 2,6-二甲基吡啶 、 potassium carbonate 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 methyl (2R,3S)-2-(tert-butoxycarbonylamino)-3-(tert-butyldimethylsilyloxy)butanoate
  参考文献：
  名称：

  De Novo Synthetic Approach to 2,4-Diamino-2,4,6-trideoxyhexoses (DATDH): Bacterial and Rare Deoxy-Amino Sugars

  摘要：

  DOI：

  10.1021/acs.orglett.3c03106

文献信息

• Synthesis of β- and γ-Hydroxy α-Amino Acids via Enzymatic Kinetic Resolution and Cyanate-to-Isocyanate Rearrangement
  作者：Piotr Szcześniak、Agnieszka Październiok-Holewa、Urszula Klimczak、Sebastian Stecko

  DOI：10.1021/jo502026a

  日期：2014.12.5

  for stereoselective preparation of all four isomers of β- and γ-hydroxy α-amino acids is presented. The developed procedure is based on enzymatic kinetic resolution and cyanate-to-isocyanate rearrangement as key steps. Stereocontrol is achieved by proper choice of the starting hydroxyacid, the course of kinetic resolution, and the stereospecific sigmatropic rearrangement step, which proceeds with full

  提出了立体选择性制备β-和γ-羟基α-氨基酸的所有四个异构体的新策略。所开发的程序是基于酶促动力学拆分和氰酸酯至异氰酸酯重排的关键步骤。立体控制是通过动力学拆分的起始羟基酸，该课程的适当选择，和立体特异性σ重排步骤，其与完整的手性转移进行实现。
• Novel Angular Benzophenazines:  Dual Topoisomerase I and Topoisomerase II Inhibitors as Potential Anticancer Agents
  作者：Nigel Vicker、Luke Burgess、Irina S. Chuckowree、Rory Dodd、Adrian J. Folkes、David J. Hardick、Timothy C. Hancox、Warren Miller、John Milton、Sukhjit Sohal、Shouming Wang、Stephen P. Wren、Peter A. Charlton、Wendy Dangerfield、Chris Liddle、Prakash Mistry、Alistair J. Stewart、William A. Denny

  DOI：10.1021/jm010329a

  日期：2002.1.1

  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.