tert-butyl (S)-(1-((tert-butyldiphenylsilyl)oxy)-3-hydroxypropan-2-yl)carbamate | 469886-48-4

• 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: tert-butyl (S)-(1-((tert-butyldiphenylsilyl)oxy)-3-hydroxypropan-2-yl)carbamate
• 英文别名: tert-butyl N-[(2S)-1-[tert-butyl(diphenyl)silyl]oxy-3-hydroxypropan-2-yl]carbamate
• CAS: 469886-48-4
• 化学式: C₂₄H₃₅NO₄Si
• 分子量: 429.632
• InChiKey: BDIWPPCRFYTGSZ-IBGZPJMESA-N

物化性质

• 熔点：
  72-73 °C
• 沸点：
  520.0±50.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-(1-((tert-butyldiphenylsilyl)oxy)-3-hydroxypropan-2-yl)carbamate 在 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 10.5h， 生成 2-[(tert-butyloxycarbonyl)amino]-3-[N3-benzoyl(thymin-1-yl)]-L-propan-1-ol
  参考文献：
  名称：

  Simple molecular engineering of glycol nucleic acid: Progression from self-pairing to cross-pairing with cDNA and RNA

  摘要：

  The acyclic chiral nucleic acid analogue, Glycol Nucleic Acid (GNA), displayed exceptional structural simplicity and atom economy while forming self-paired duplexes, using canonical Watson-Crick base pairing. We disclose here that the replacement of phosphodiester linker in GNA with somewhat rigid and shorter carbamate linker in Glycol Carbamate Nucleic Acid (GCNA) backbone allows unprecedented stability to the antiparallel self-paired duplexes. The R-GCNA oligomers were further found to form cross-paired antiparallel duplexes with cDNA and RNA following Watson-Crick base pairing. The stability of cross-paired GCNA: DNA and GCNA: RNA duplexes was higher than the corresponding DNA: DNA and DNA: RNA duplexes. The chiral (R) and (S) precursors were easily accessible from naturally occurring L-serine. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.08.022
• 作为产物：
  描述：

  2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester 在 咪唑 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 tert-butyl (S)-(1-((tert-butyldiphenylsilyl)oxy)-3-hydroxypropan-2-yl)carbamate
  参考文献：
  名称：

  [EN] FUSED RING KRAS INHIBITORS FOR TREATING DISEASE
  [FR] INHIBITEURS DE KRAS À CYCLES FUSIONNÉS POUR LE TRAITEMENT D'UNE MALADIE

  摘要：

  The present disclosure relates to fused ring compounds targeting KRAS, pharmaceutical compositions containing the compounds, and methods of using such compounds to treat disease, such as cancer.

  公开号：

  WO2024015262A1

文献信息

• Pseudoenantiomeric glycoclusters: synthesis and testing of heterobivalency in carbohydrate–protein interactions
  作者：Jasna Brekalo、Guillaume Despras、Thisbe K. Lindhorst

  DOI：10.1039/c9ob00124g

  日期：——

  ligands to obtain a library of pseudoenantiomeric glycoclusters. They all have an α-d-mannosyl residue in common as a specific ligand for lectins FimH and ConA, while they differ in the second carbohydrate portion, consisting of a β-d-glucosyl, a β-d-galactosyl or a β-d-glucosaminyl residue as unspecific ligands. The synthesised heteroclusters were tested in standard binding-inhibition assays investigating

  多价碳水化合物与蛋白质的相互作用是细胞识别过程中的关键事件，并且已经通过合成糖模拟物进行了广泛研究。迄今为止，在多价结构的设计中经常考虑化合价，即与多价支架连接的配体的多重性，但是这些研究并未在分子水平上导致对聚糖识别的结论性理解。在这项工作中，我们通过设计第一个杂二价非对映异构糖簇为碳水化合物-凝集素识别研究增加了一个新的方面，以便研究杂多价和相对配体取向的影响。将分别衍生自d-丝氨酸和l-丝氨酸的两个对映体支架用两个不同的碳水化合物配体糖基化以获得假对映体糖簇库。它们都具有作为凝集素FimH和ConA特异性配体的α-d-甘露糖基残基，而它们在第二个碳水化合物部分（由β-d-葡萄糖基，β-d-半乳糖基或β- d-氨基葡萄糖残基为非特异性配体。在研究FimH介导的细菌粘附和ConA与甘露糖基化表面结合的标准结合抑制试验中测试了合成的异源团簇。观察到两种含假对映异构体葡萄糖的糖簇作为FimH
• Total Syntheses and Biological Activities of Vinylamycin Analogues
  作者：Jinghan Wang、Beijia Kuang、Xiaoqian Guo、Jianwei Liu、Yahui Ding、Jiangnan Li、Shende Jiang、Ying Liu、Fang Bai、Luyuan Li、Quan Zhang、Xiao-Yu Zhu、Bo Xia、Chun-Qi Li、Liang Wang、Guang Yang、Yue Chen

  DOI：10.1021/acs.jmedchem.6b01745

  日期：2017.2.9

  reported to be an antibiotic previously. Herein we report vinylamycin to be active against K562 leukemia cells (IC50 = 4.86 μM) and be unstable in plasma (t1/2 = 0.54 h). A total of 24 vinylamycin analogues with modification of the OH group and chiral centers were generated via a combinatorial approach. The lead compound 1a was subsequently characterized as having the following: no antimicrobial activity

  以前有报道称天然的二肽肽乙烯基霉素是一种抗生素。在此，我们报道乙烯基霉素对K562白血病细胞有活性（IC 50 = 4.86μM ），在血浆中不稳定（t 1/2 = 0.54 h）。通过组合方法产生了总共24个具有OH基团和手性中心修饰的乙烯基霉素类似物。铅化合物1a随后具有以下特征：无抗菌活性，明显更高的血浆稳定性（t 1/2 = 14.3 h），对K562白血病细胞的活性得到改善（IC 50 = 0.64μM）和高达75％的细胞在K562细胞异种移植斑马鱼模型中没有明显的毒性。此外，复合图1a在低氧条件下维持其对乳腺癌细胞MCF-7的活性。相比之下，在相同的低氧MCF-7细胞体外模型中，吉西他滨的活性低15倍。因此，本结果证明1a具有作为抗癌剂的巨大潜力。
• [EN] CYCLIC PEPTIDE ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES PEPTIDIQUES CYCLIQUES
  申请人：GENENTECH INC

  公开号：WO2020185999A1

  公开（公告）日：2020-09-17

  Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of lipoprotein signal peptidase II (LspA), a key protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

  本发明提供了抗菌化合物，其中在某些实施例中，这些化合物具有广谱生物活性。在各种实施例中，这些化合物通过抑制细菌中的关键蛋白质——脂蛋白信号肽酶II（LspA）发挥作用。还提供了使用本发明所述化合物的药物组合物和治疗方法。
• Orthogonally protected glycerols and 2-aminodiols, useful building blocks in heterocyclic chemistry
  作者：Isabelle Canet、Marie-Eve Sinibaldi、Anthony Ollivier、Marlène Goubert、Ahmatjan Tursun

  DOI：10.3998/ark.5550190.0011.910

  日期：——

  The efficient synthesis of orthogonally protected glycerols, 2-aminopropane-1,3-diols and 2aminobutane-1,4-diols that can constitute useful tools in heterocyclic chemistry, is reported. These interesting tri-functionalized small synthons were easily prepared from serine or aspartic acid. In addition, these substrates can be readily transformed into their iodide derivatives in very good yields.

  报告了正交保护的甘油、2-氨基丙烷-1,3-二醇和 2-氨基丁烷-1,4-二醇的有效合成，它们可以构成杂环化学中的有用工具。这些有趣的三功能化小合成子很容易从丝氨酸或天冬氨酸制备。此外，这些底物可以很容易地以非常好的产率转化为它们的碘化物衍生物。
• Synthesis of a Polymer-Supported Oxazolidine Aldehyde for Asymmetric Chemistry
  作者：A. Jonathan Wills、Yamuna Krishnan-Ghosh、Shankar Balasubramanian

  DOI：10.1021/jo0203239

  日期：2002.9.1

  An expedient synthesis of the polymer-supported aldehyde 3, as a Garner aldehyde equivalent, is described. Oxazolidine 3 may be obtained through preformation of aldehyde linker 4 in solution and loaded onto amine-terminating resin under peptide-coupling conditions, or alternatively via oxidation of polymer-bound alcohol 14. The integrity of the serine-derived stereocenter is maintained through all steps of the synthesis.