5-[3-(tert-butyldimethylsilyloxy)-propane-1-sulfonyl]-1-phenyl-1H-tetrazole | 519002-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-[3-(tert-butyldimethylsilyloxy)-propane-1-sulfonyl]-1-phenyl-1H-tetrazole
• 英文别名: 5-((3-((tert-butyldimethylsilyl)oxy)propyl)sulfonyl)-1-phenyl-1H-tetrazole；Tert-butyl-dimethyl-[3-(1-phenyltetrazol-5-yl)sulfonylpropoxy]silane
• CAS: 519002-88-1
• 化学式: C₁₆H₂₆N₄O₃SSi
• 分子量: 382.559
• InChiKey: QEMAROPUMJWAPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  488.8±47.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  95.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[3-(tert-butyldimethylsilyloxy)-propane-1-sulfonyl]-1-phenyl-1H-tetrazole 在 四氯化钛 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  天然6-氯四氢呋喃产乙酸原素的两种可能的非对映异构体的全合成及其立体结构阐明

  摘要：

  天然6-氯四氢呋喃产乙酸原1的两种可能的非对映异构体的首次全合成已经完成。合成路线设有-5-外- TET环合，ž选择性Wittig反应和Julia烯为共轭二烯和烯炔部分和立体选择性氯化的结构。通过比较其1 H和13 C NMR数据以及比旋光度与天然产物的比旋光度，可以阐明天然（-）-6-氯四氢呋喃产乙酸原蛋白1的绝对构型。

  DOI：

  10.1002/chem.201703234
• 作为产物：
  描述：

  3-(叔丁基二甲基硅氧)丙醇 在 碳酸氢钠 、 间氯过氧苯甲酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.67h， 生成 5-[3-(tert-butyldimethylsilyloxy)-propane-1-sulfonyl]-1-phenyl-1H-tetrazole
  参考文献：
  名称：

  Sanglifehrin−Cyclophilin Interaction:  Degradation Work, Synthetic Macrocyclic Analogues, X-ray Crystal Structure, and Binding Data

  摘要：

  Sanglifehrin A (SFA) is a novel immunosuppressive natural product isolated from Streptomyces sp. A92-308110. SFA has a very strong affinity for cyclophilin A (IC50 = 6.9 +/- 0.9 nM) but is structurally different from cyclosporin A (CsA) and exerts its immunosuppressive activity via a novel mechanism. SFA has a complex molecular structure consisting of a 22-membered macrocycle, bearing in position 23 a nine-carbon tether terminated by a highly substituted spirobicyclic moiety. Selective oxidative cleavage of the C-26=C-27 exocyclic double bond affords the spirolactam containing fragment 1 and macrolide 2. The affinity of 2 for cyclophilin (IC50 = 29 +/- 2.1 nM) is essentially identical to SFA, which indicates that the interaction between SFA and cyclophilin A is mediated exclusively by the macrocyclic portion of the molecule. This observation was confirmed by the X-ray crystal structure resolved at 2.1 Angstrom of cyclophilin A complexed to macrolide 16, a close analogue of 2. The X-ray crystal structure showed that macrolide 16 binds to the same deep hydrophobic pocket of cyclophilin A as CsA. Additional valuable details of the structure-activity relationship were obtained by two different chemical approaches: (1) degradation work on macrolide 2 or (2) synthesis of a library of macrolide analogues using the ring-closing metathesis reaction as the key step. Altogether, it appears that the complex macrocyclic fragment of SFA is a highly optimized combination of multiple functionalities including an (E,E)-diene, a short polypropionate fragment, and an unusual tripeptide unit, which together provide an extremely strong affinity for cyclophilin A.

  DOI：

  10.1021/ja021327y

文献信息

• Stereoselective Synthesis of (S,E)-2-(trimethylsilyl)ethyl 3-hydroxy-7- (tritylthio)hept-4-enoate
  作者：Zhiyi Yao、Xin Zeng、Wei Yi、Sheng Jiang

  DOI：10.2174/157017811794557868

  日期：2011.1.1

  (S,E)-2-(trimethylsilyl)ethyl 3-hydroxy-7-(tritylthio)hept-4-enoate was synthesized from commercially available L-malic acid by the Julia-Kocienski olefination coupling method. This method provides a concise synthetic strategy for (S,E) -3-hydroxy-7-mercaptohept-4-enoic acid.

  (S,E)-2-(三甲基硅基)乙基 3-羟基-7-(三苯甲硫基)庚-4-烯酸酯是通过商业可得的L-苹果酸，采用Julia-Kocienski 烯化偶联方法合成的。该方法为(S,E)-3-羟基-7-巯基庚-4-烯酸提供了一种简洁的合成策略。
• Synthesis and structure–activity relationship study of FD-891: importance of the side chain and C8–C9 epoxide for cytotoxic activity against cancer cells
  作者：Tomohiro Itagaki、Ayano Kawamata、Miho Takeuchi、Keisuke Hamada、Yoshiharu Iwabuchi、Tadashi Eguchi、Fumitaka Kudo、Takeo Usui、Naoki Kanoh

  DOI：10.1038/ja.2015.148

  日期：2016.4

  Unified synthesis of FD-891 analogs and their structure-activity relationship are described. By using stereoselective allylation/crotylation and Evans aldol chemistry, six side-chain fragments having different length and terminus were synthesized. These fragments were coupled with a macrolactone fragment, improved synthesis of which was also developed here, to generate FD-891 and five truncated analogs

  描述了FD-891类似物的统一合成及其构效关系。通过使用立体选择性烯丙基化/丁酰化和Evans aldol化学，合成了六个具有不同长度和末端的侧链片段。这些片段与大内酯片段偶联，在此也开发了大内酯片段的合成方法，以生成FD-891和五个截短的类似物。测试了这些合成化合物以及从基因破坏的链霉菌链霉菌突变体的发酵中获得的三种类似物的体外抗HeLa细胞的细胞毒活性。结果，发现C8-C9环氧化物和侧链末端的共存对于细胞毒性活性至关重要。
• Role of the Backbone Conformation at Position 7 in the Structure and Activity of Marinostatin, an Ester-Linked Serine Protease Inhibitor
  作者：Misako Taichi、Toshimasa Yamazaki、Yuji Nishiuchi

  DOI：10.1002/cbic.201200315

  日期：2012.9.3

  Rational design of inhibitors: The cis‐amide backbone at position 7 in the serine protease inhibitor marinostatin was replaced with an E or Z olefin. The E olefin analogue was not active, but the Z analogue was. The cis conformation might play a critical role in organizing a canonical structure for binding to proteases.

  抑制剂的合理设计：丝氨酸蛋白酶抑制剂marinostatin 7位的顺式酰胺骨架被E或Z烯烃取代。该Ë烯烃模拟并不活跃，但ž模拟了。该顺构象可能在组织的规范结构结合蛋白酶发挥关键作用。
• Identification by Synthesis: Imidacins, Urocanate-Derived Alkaloids from the Myxobacterium Stigmatella aurantiaca
  作者：Michael Kostka、Daniel Krug、Jennifer Herrmann、Jeroen S. Dickschat、Julia Meyer、Rolf Müller、Stefan Schulz

  DOI：10.1021/acs.orglett.4c02036

  日期：2024.8.2

  screens and allowing hitherto unseen compounds to be uncovered from previously investigated producers. In line with these trends, we report here imidacins, a novel class of secondary metabolites specific to the myxobacterial genus Stigmatella. A combination of secondary metabolome analysis, genome-mining techniques, spectroscopic analysis, and finally total synthesis was used to allow structure elucidation

  基因组挖掘和代谢组学启发的方法等创新发现方法重塑了天然产物研究领域，补充了传统的基于生物活性的筛选，并允许从先前研究的生产者中发现迄今为止未见的化合物。根据这些趋势，我们在此报告了咪达星，这是粘细菌属Stigmatella特有的一类新型次生代谢产物。结合二级代谢组分析、基因组挖掘技术、光谱分析和最后的全合成来阐明结构。咪达星是尿刊酸衍生的脂肪酸，具有相邻的环丙烷部分，其结构特征是迄今为止天然产物中前所未有的。
• WO2019199667A5
  申请人：——

  公开号：WO2019199667A5

  公开（公告）日：2022-04-15