2-(tert-butyldimethylsilyloxy)but-3-enyl-4-methylbenzenesulfonate | 881383-26-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(tert-butyldimethylsilyloxy)but-3-enyl-4-methylbenzenesulfonate
• 英文别名: 2-O-tert-butyldimethylsilyl-3-butene-1-(p-toluenesulfonate)；2-((tert-butyldimethylsilyl)oxy)but-3-en-1-yl 4-methylbenzenesulfonate；2-[Tert-butyl(dimethyl)silyl]oxybut-3-enyl 4-methylbenzenesulfonate；2-[tert-butyl(dimethyl)silyl]oxybut-3-enyl 4-methylbenzenesulfonate
• CAS: 881383-26-2
• 化学式: C₁₇H₂₈O₄SSi
• 分子量: 356.558
• InChiKey: GSFNRXFCBRMPQW-UHFFFAOYSA-N

物化性质

• 沸点：
  418.0±40.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(tert-butyldimethylsilyloxy)but-3-enyl-4-methylbenzenesulfonate 在 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 195.0h， 生成 1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-3-(2-((tert-butyldimethylsilyl)oxy)but-3-en-1-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and Mutagenesis of the Butadiene-Derived N3 2‘-Deoxyuridine Adducts

  摘要：

  1,3-Butadiene is a known carcinogen and mutagen that acts through a variety of metabolic intermediates that react with DNA, forming stable and unstable lesions on dG, dA, dC, and dT. The N3 2'-deoxyuridine adducts are a highly stable, stereoisomeric mixture of adducts derived from the reaction of cytosine with the monoepoxide metabolite of butadiene, followed by spontaneous deamination. In this study, the phosphoramidites and subsequent oligodeoxynucleotides containing the N3 2'-deoxyuridine adducts have been constructed and characterized. Using a single-stranded shuttle vector DNA, the mutagenic potential of these adducts has been tested following replication in mammalian cells. Replication past the N3 2'-deoxyuridine adducts was found to be highly mutagenic with an overall mutation yield of similar to 97%. The major mutations that were observed were C to T transitions and C to A transversions. In vitro, these adducts posed a complete block to both the Klenow fragment of Escherichia coli polymerase I and polymerase epsilon, while these lesions significantly blocked polymerase delta. These data suggested a possible involvement of bypass polymerases in the in vivo replication of these lesions. Overall, these findings indicate that the N3 2'-deoxyuridine adducts are highly mutagenic lesions that may contribute to butadiene-mediated carcinogenesis.

  DOI：

  10.1021/tx060016o
• 作为产物：
  描述：

  对甲苯磺酰氯 在 咪唑 、 二正丁基氧化锡 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 32.0h， 生成 2-(tert-butyldimethylsilyloxy)but-3-enyl-4-methylbenzenesulfonate
  参考文献：
  名称：

  CDPK1 INHIBITORS, COMPOSITIONS, AND METHODS RELATED THERETO

  摘要：

  该发明涉及钙依赖性蛋白激酶1（CDPK1）的抑制剂及其药物制剂。该发明进一步涉及使用该发明的新型抑制剂治疗寄生虫感染的方法，例如弓形虫、疟原虫、人类小肠球虫或小肠球小弓形虫感染。

  公开号：

  US20210347780A1

文献信息

• Enantioselective Synthesis of Cyclic, Quaternary Oxonitriles
  作者：Yakup Güneş、M. Fatih Polat、Ertan Sahin、Fraser F. Fleming、Ramazan Altundas

  DOI：10.1021/jo1011202

  日期：2010.11.5

  Quaternary oxonitriles are stereoselectively generated from the union of five-, six-, and seven-membered 2-chloroalkenecarbonitriles with chiral alcohols via a Claisen rearrangement. The strategy rests on a new conjugate addition−elimination of allylic alkoxides to 2-chlorocycloalkenecarbonitriles to afford substituted 2-alkoxyalkenenitriles. Subsequent thermolysis unmasks a cyclic oxonitrile while

  五元，六元和七元的2-氯烯烃腈与手性醇通过克莱森重排的结合立体选择性地生成季腈。该策略基于新的共轭加成-将烯丙基醇盐消除到2-氯环烯腈中，得到取代的2-烷氧基烯腈。随后的热解反应会掩盖环状氧腈，同时选择性地形成对映体比率通常大于9：1的新季铵中心。整体烷基化策略解决了对映选择性地生成受阻的四级中心同时安装酮，腈和烯烃官能团的挑战。
• Iron(III)-Catalyzed Consecutive Aza-Cope−Mannich Cyclization: Synthesis of <i>trans</i>-3,5-Dialkyl Pyrrolidines and 3,5-Dialkyl-2,5-dihydro-1<i>H</i>-pyrroles
  作者：Rubén M. Carballo、Martín Purino、Miguel A. Ramírez、Víctor S. Martín、Juan I. Padrón

  DOI：10.1021/ol102372c

  日期：2010.11.19

  efficient alkene aza-Cope−Mannich cyclization between 2-hydroxy homoallyl tosylamine and aldehydes in the presence of iron(III) salts to obtain 3-alkyl-1-tosyl pyrrolidines in good yields is described. The process is based on the consecutive generation of a γ-unsaturated iminium ion, 2-azonia-[3,3]-sigmatropic rearrangement, and further intramolecular Mannich reaction. Iron(III) salts are also shown to be

  描述了在铁（III）盐存在下2-羟基高烯丙基甲苯磺胺和醛之间的有效的烯烃氮杂-Cope-Mannich环化反应，以高收率获得3-烷基-1-甲苯基吡咯烷。该过程基于连续生成的γ-不饱和亚胺离子，2-氮杂-[3,3]-σ重排以及进一步的分子内曼尼希反应。铁（III）盐也被证明是使用2-羟基高炔丙基甲苯磺胺的新型aza-Cope-Mannich环化反应的优异催化剂。
• Synthesis of methyl 2-oxo-5-vinyl-2,5-tetrahydrofuran-3-carboxylate
  作者：Maximilian A. Silvestri、Chang He、Anita Khoram、Salvatore D. Lepore

  DOI：10.1016/j.tetlet.2005.12.114

  日期：2006.3

  A synthesis of methyl 2-oxo-5-vinyl-tetrahydrofuran-3-carboxylate involving five synthetic steps from commercially available 3,4-dihydroxybutene is reported. (c) 2006 Elsevier Ltd. All rights reserved.
• CDPK1 INHIBITORS, COMPOSITIONS, AND METHODS RELATED THERETO
  申请人：Vyera Pharmaceuticals, LLC

  公开号：US20210347780A1

  公开（公告）日：2021-11-11

  The invention relates to inhibitors of calcium-dependent protein kinase 1 (CDPK1) and pharmaceutical preparations thereof. The invention further relates to methods of treatment of parasitic infections, such as T. gondii, P. falciparum, C. hominis , or C. parvum infections, using the novel inhibitors of the invention.

  该发明涉及钙依赖性蛋白激酶1（CDPK1）的抑制剂及其药物制剂。该发明进一步涉及使用该发明的新型抑制剂治疗寄生虫感染的方法，例如弓形虫、疟原虫、人类小肠球虫或小肠球小弓形虫感染。
• Synthesis and Mutagenesis of the Butadiene-Derived N3 2‘-Deoxyuridine Adducts
  作者：Priscilla H. Fernandes、Linda C. Hackfeld、Ivan D. Kozekov、Richard P. Hodge、R. Stephen Lloyd

  DOI：10.1021/tx060016o

  日期：2006.7.1

  1,3-Butadiene is a known carcinogen and mutagen that acts through a variety of metabolic intermediates that react with DNA, forming stable and unstable lesions on dG, dA, dC, and dT. The N3 2'-deoxyuridine adducts are a highly stable, stereoisomeric mixture of adducts derived from the reaction of cytosine with the monoepoxide metabolite of butadiene, followed by spontaneous deamination. In this study, the phosphoramidites and subsequent oligodeoxynucleotides containing the N3 2'-deoxyuridine adducts have been constructed and characterized. Using a single-stranded shuttle vector DNA, the mutagenic potential of these adducts has been tested following replication in mammalian cells. Replication past the N3 2'-deoxyuridine adducts was found to be highly mutagenic with an overall mutation yield of similar to 97%. The major mutations that were observed were C to T transitions and C to A transversions. In vitro, these adducts posed a complete block to both the Klenow fragment of Escherichia coli polymerase I and polymerase epsilon, while these lesions significantly blocked polymerase delta. These data suggested a possible involvement of bypass polymerases in the in vivo replication of these lesions. Overall, these findings indicate that the N3 2'-deoxyuridine adducts are highly mutagenic lesions that may contribute to butadiene-mediated carcinogenesis.