PEG 4000-sulfonyl chloride

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: PEG 4000-sulfonyl chloride
• 英文别名: sulfonyl chloride resin；[(2R,3S,4E,7R,9R,10R,11S,12S,13R)-10-[(2S,3R,4S,6R)-4-(dimethylamino)-6-methyl-3-trimethylsilyloxyoxan-2-yl]oxy-2-ethyl-9-methoxy-12-[(2R,4R,5S,6S)-4-methoxy-4,6-dimethyl-5-trimethylsilyloxyoxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-6,14-dioxo-1-oxacyclotetradec-4-en-3-yl] imidazole-1-carboxylate
• 化学式: ClO₂PolS
• 分子量: 968.4
• InChiKey: DXMDSPSNBYQWIM-GATIUUODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.0
• 重原子数：
  66
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  165
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  PEG 4000-sulfonyl chloride 、 1,3-丁二醇 在 吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Thiopyrophosphoantigens: Solid-phase Synthesis and in Vitro Characterization of a New Class of Vγ9 Vδ2 T Cells Activators

  摘要：

  The V gamma 9 V delta 2 T cells mediate rapid, innate-like immune responses to pathogens and are important in several key immunoregulatory pathways, including those involved in infections and tumor development. V gamma 9 V delta 2 T cells respond to low molecular weight isoprenoid phosphoantigens; the prototypic stimulatory compound is isopentenylpyrophosphate (IPP), an alkylphosphate intermediate of mevalonate metabolism that elicits proliferative, cytotoxic, and cytokine secretion responses. We studied the replacement of the pyrophosphate moiety with the thiopyrophosphate bioisostere, synthesizing thioanalogues of IPP and 4-hydroxy-3-methyl-but-2-enyl pyrophosphate (HMBPP, the most potent natural antigen known to date). Once their in vitro efficacy and stability had been demonstrated, we synthesized a small library of compounds through the development of an innovative solid-phase strategy. Biological results confirmed thioHMBPP to be the best compound of this first series. Future aims are (i) the exploitation of the parallel solid-phase strategy to further explore structure-activity relationships of this new class of synthetic antigens and (ii) the determination of the PK/PD profile of thioHMBPP.

  DOI：

  10.1021/jm900054u
• 作为产物：
  描述：

  6-O-Methyl-2',4''-O-bis(trimethylsilyl)erythromycin A 、 N,N'-羰基二咪唑 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 生成 PEG 4000-sulfonyl chloride
  参考文献：
  名称：

  WO2008/23383

  摘要：

  公开号：
• 作为试剂：
  描述：

  对甲基苯磺酰异氰酸酯 、 1,2-丁二醇 在 PEG 4000-sulfonyl chloride 、 敌草腈 、 三乙胺 作用下， 生成 5-ethyl-3-tosyl-1,3-oxazolidin-2-one 、 N-(4-toluenesulfonyl)-4-ethyl-2-oxazolidone
  参考文献：
  名称：

  Solid-phase synthesis of 3,5-disubstituted 1,3-oxazolidin-2-ones by an activation/cyclo-elimination process

  摘要：

  Polymer-supported sulfonyl chloride is used in the solid-phase synthesis of disubstituted 1,3-oxazolidin-2-ones. The target compounds were prepared by attaching 1,2-diols to the solid support, followed by reaction with p-toluenesulfonyl isocyanate and subsequent cycle-elimination with concurrent detachment from the resin. Oxazolidinones of high enantiopurity can be prepared with this method by employing enantiopure 1,2-diols. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01608-6

文献信息

• Liquid-Phase Organic Synthesis of imidazo[1,2-<i>a</i>]pyridine Derivatives Using PEG-Supported Sulfonyl Chloride
  作者：Chao-Li Wang、Shou-Ri Sheng、Hu Chen、Xiao-Ling Liu、Ming-Zhong Cai

  DOI：10.3184/030823408x320638

  日期：2008.5

  Reaction of PEG-bound sulfonic acid with thionyl chloride formed the difunctionalised PEG-supported sulfonyl chloride, which was treated with α-hydroxyketones, followed by treatment with 2-aminopyridine in the presence of potassium carbonate efficient to afford imidazo[1,2-a]pyridines in good yields with a facile work-up procedure.

  PEG 结合的磺酸与亚硫酰氯反应形成双官能化 PEG 负载的磺酰氯，用 α-羟基酮处理，然后在碳酸钾存在下用 2-氨基吡啶处理，有效地得到咪唑[1,2-a ] 吡啶以良好的收率与简单的后处理程序。
• Acyclic and cyclic thioenamino peptides: solution- and solid-phase synthesis
  作者：Lee Goren、Doron Pappo、Israel Goldberg、Yoel Kashman

  DOI：10.1016/j.tetlet.2008.12.072

  日期：2009.3

  potential γ-turn mimetic), were synthesized, and the structure of 11 was secured by X-ray diffraction analysis of its TFA salt. The aforementioned compounds were prepared in solution and by solid-phase synthesis. Additionally, we have prepared thioenamino diketopiperazine synthon 16.

  合成了7元和10元环硫烯氨基肽，即1,4-噻唑酮（11）和环硫烯氨基肽9（代表潜在的γ-转角模拟物），并通过X-固定了11的结构的TFA盐的X射线衍射分析。上述化合物是在溶液中并通过固相合成制备的。此外，我们还准备了thioenamino diketopiperazine synthon 16。
• WO2008/8059
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2008/23383
  申请人：——

  公开号：——

  公开（公告）日：——
• Thiopyrophosphoantigens: Solid-phase Synthesis and in Vitro Characterization of a New Class of Vγ9 Vδ2 T Cells Activators
  作者：Perla Breccia、Francesca Angeli、Ilaria Cerbara、Alessandra Topai、Giovanni Auricchio、Angelo Martino、Vittorio Colizzi、Fabrizio Poccia

  DOI：10.1021/jm900054u

  日期：2009.6.25

  The V gamma 9 V delta 2 T cells mediate rapid, innate-like immune responses to pathogens and are important in several key immunoregulatory pathways, including those involved in infections and tumor development. V gamma 9 V delta 2 T cells respond to low molecular weight isoprenoid phosphoantigens; the prototypic stimulatory compound is isopentenylpyrophosphate (IPP), an alkylphosphate intermediate of mevalonate metabolism that elicits proliferative, cytotoxic, and cytokine secretion responses. We studied the replacement of the pyrophosphate moiety with the thiopyrophosphate bioisostere, synthesizing thioanalogues of IPP and 4-hydroxy-3-methyl-but-2-enyl pyrophosphate (HMBPP, the most potent natural antigen known to date). Once their in vitro efficacy and stability had been demonstrated, we synthesized a small library of compounds through the development of an innovative solid-phase strategy. Biological results confirmed thioHMBPP to be the best compound of this first series. Future aims are (i) the exploitation of the parallel solid-phase strategy to further explore structure-activity relationships of this new class of synthetic antigens and (ii) the determination of the PK/PD profile of thioHMBPP.