tert-butyl (2S)-1-hydroxy-3-oxobutan-2-ylcarbamate | 1013028-29-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl (2S)-1-hydroxy-3-oxobutan-2-ylcarbamate
• 英文别名: 1,1-Dimethylethyl N-[(1R)-1-(hydroxymethyl)-2-oxopropyl]carbamate；tert-butyl N-[(2R)-1-hydroxy-3-oxobutan-2-yl]carbamate
• CAS: 1013028-29-9
• 化学式: C₉H₁₇NO₄
• 分子量: 203.238
• InChiKey: FYWDYTKRLCAHLY-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-1-hydroxy-3-oxobutan-2-ylcarbamate 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 42.0h， 生成 (S)-methyl N-(tert-butoxycarbonyl)-2-amino-3-(dimethylphosphono)propanoate
  参考文献：
  名称：

  探索用于抑制剂设计的 HIV-1 逆转录酶的 dNTP 结合位点

  摘要：

  HIV-1 逆转录酶 (RT) 在病毒生命周期中发挥着核心作用，FDA 批准的抗 HIV 药物中大约有一半针对 RT。核苷类似物 (NRTIs) 需要细胞磷酸化才能与 RT 结合，为了绕过这个限速路径，我们设计了一系列新的无环磷酸核苷类似物作为三磷酸核苷模拟物，旨在螯合催化 Mg 2+离子通过膦酸盐和/或羧酸基团。开发了新的合成程序来获取这些核苷膦酸盐类似物。与 HIV-1 RT/dsDNA 复合的 X 射线结构表明它们的结合模式与我们之前报道的化合物系列的结合模式不同。讨论了链长、手性和接头原子的影响。对这些新化合物的详细结构了解为设计新型 HIV-1 RT 抑制剂提供了机会。

  DOI：

  10.1016/j.ejmech.2021.113785
• 作为产物：
  描述：

  (R)-4-乙酰基-2,2-二甲基噁唑烷-3-羧酸叔丁酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以85%的产率得到tert-butyl (2S)-1-hydroxy-3-oxobutan-2-ylcarbamate
  参考文献：
  名称：

  An improved method for culturing Streptomyces sahachiroi: Biosynthetic origin of the enol fragment of azinomycin B

  摘要：

  Azinomycin B is an environmental DNA crosslinking agent produced by the soil microorganism Streptomyces sahachiroi. While the agent displays potent cytotoxic activities against leukemic cell lines and animal mouse models, the lack of a consistent supply of the natural product has hampered detailed biological investigations on the compound, including its mode of action and biosynthesis. We report here a significant methodological improvement in the culturing of the bacterium, which allows reliable and steady production of the natural product in good yields. The key experimental step involves the culturing of the strain on dehydrated plates, followed by the generation of a two-stage starter culture and subsequent fermentation of the strain under nutrient-starved conditions. We illustrate use of this culture system by investigating the formation of the enol fragment of the molecule in isotopic labeling experiments with threonine and several advanced precursors (beta-ketoamino acid 3, beta-hydroxyamino aldehyde 4, and beta-ketoaminoaldehyde 5). The results unequivocally show that threonine is the most advanced precursor accepted by the NRPS (non-ribosomal peptidyl synthetase) machinery for final processing and construction of the enol moiety of the natural product. (C) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2007.08.002

文献信息

• [EN] PROCESS FOR PREPARATION OF LACOSAMIDE AND SOME N-BENZYL-PROPANAMIDE INTERMEDIATE DERIVATIVES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE LACOSAMIDE ET DE DÉRIVÉS INTERMÉDIAIRES DE N-BENZYL-PROPANAMIDE
  申请人：INDOCO REMEDIES LTD

  公开号：WO2012014226A1

  公开（公告）日：2012-02-02

  The present invention discloses novel process for the preparation of (2R)-2-acetamido-N- benzyl-3-methoxypropanamide of Formula I involving novel intermediates of Formula - XIX and Formula - XX.

  本发明公开了一种制备（2R）-2-乙酰氨基-N-苄基-3-甲氧基丙酰胺（化学式I）的新工艺，涉及到新中间体化合物XIX和XX的制备。
• [EN] ALPHA-AMINO AMIDE DERIVATIVES<br/>[FR] DÉRIVÉS D'ALPHA-AMINO-AMIDE
  申请人：TAISHO PHARMA CO LTD

  公开号：WO2018216823A1

  公开（公告）日：2018-11-29

  Provided are novel compounds represented by the following general formula [1] or pharmaceutically acceptable salts thereof, that inhibit LpxC, as well as pharmaceutical drugs comprising those compounds or pharmaceutically acceptable salts thereof, that exhibit antimicrobial activity against gram-negative bacteria including Pseudomonas aeruginosa and their drug resistant strains and are useful in the treatment of bacterial infections, wherein X is selected from the following formula [2] : Y is selected from the following formula [3].

  提供以下一般式[1]所代表的新化合物或其药用盐，其抑制LpxC，以及包含这些化合物或其药用盐的药物，对包括铜绿假单胞菌及其耐药菌株在内的革兰氏阴性细菌表现出抗微生物活性，并且在治疗细菌感染方面有用，其中X从以下一般式[2]中选择：Y从以下一般式[3]中选择。
• Compounds Active in Sphingosine 1-Phosphate Signaling
  申请人：Lynch R. Kevin

  公开号：US20070219163A1

  公开（公告）日：2007-09-20

  The present invention relates to S1P analogs that have activity as S1P receptor modulating agents and the use of such compounds to treat diseases associated with inappropriate S1P receptor activity. The compounds have the general structure: wherein R 11 is C 5 -C 18 alkyl or C 5 -C 18 alkenyl; Q is C 3 -C 6 optionally substituted cycloalkyl, C 3 -C 6 optionally substituted heterocyclic, C 3 -C 6 optionally substituted aryl C 3 -C 6 optionally substituted heteroaryl or —NH(CO)—; R 3 is H, C 1 -C 4 alkyl, (C 1 -C 4 alkyl)OH or (C 1 -C 4 alkyl)NH 2 ; R 23 is H or C 1 -C 4 alkyl, and R 15 is hydroxy, phosphonate, or wherein X and R 12 is O or S; or a pharmaceutically acceptable salt or tautomer thereof.

  本发明涉及具有S1P受体调节剂活性的S1P类似物，以及使用这些化合物治疗与不适当的S1P受体活性相关的疾病。这些化合物具有以下一般结构：其中R11是C5-C18烷基或C5-C18烯基；Q是C3-C6可选取代的环烷基，C3-C6可选取代的杂环基，C3-C6可选取代的芳基，C3-C6可选取代的杂芳基或—NH（CO）—；R3是H，C1-C4烷基，（C1-C4烷基）OH或（C1-C4烷基）NH2；R23是H或C1-C4烷基，R15是羟基，膦酸酯或其中X和R12是O或S；或其药学上可接受的盐或互变异构体。
• Orally available sphingosine 1-phosphate receptor agonists and antagonists
  申请人：Lynch R. Kevin

  公开号：US20070088002A1

  公开（公告）日：2007-04-19

  The present invention relates to S1P analogs that have activity as S1P receptor modulating agents and the use of such compounds to treat diseases associated with inappropriate S1P receptor activity. The compounds have the general structure (I) wherein R 11 is C 5 -C 18 alkyl or C 5 -C 18 alkenyl; Q is selected from the group consisting of C 3 -C 6 optionally substituted cycloalkyl, C 3 -C 6 optionally substituted heterocyclic, C 3 -C 6 optionally substituted aryl C 3 -C 6 optionally substituted heteroaryl and; R 2 is selected from the group consisting of H, C 1 -C 4 alkyl, (C 1 -C 4 alkyl)OH and (C 1 -C 4 alkyl)NH 2 ; R 23 is H or C 1 -C 4 alkyl, and R 15 is a phosphonate ester or a phosphate ester or a pharmaceutically acceptable salt or tautomer thereof.

  本发明涉及具有S1P受体调节剂活性的S1P类似物，并使用这些化合物治疗与不适当S1P受体活性相关的疾病。这些化合物具有一般结构（I），其中R11为C5-C18烷基或C5-C18烯基；Q选自C3-C6可选取代的环烷基、C3-C6可选取代的杂环、C3-C6可选取代的芳基、C3-C6可选取代的杂芳基；R2选自H、C1-C4烷基、（C1-C4烷基）OH和（C1-C4烷基）NH2；R23为H或C1-C4烷基，R15为磷酸酯或磷酸酯酯或其药学上可接受的盐或互变异构体。
• PROCESS FOR PREPARATION OF LACOSAMIDE AND SOME N-BENZYL-PROPANAMIDE INTERMEDIATE DERIVATIVES
  申请人：Indoco Remedies Limited

  公开号：EP2598476B1

  公开（公告）日：2014-07-02