2-Chlormethyl-benzothiophen-dioxid-(1,1) | 101724-26-9

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2-Chlormethyl-benzothiophen-dioxid-(1,1)
• 英文别名: 2-Chloromethylbenzo[b]thiophene 1,1-dioxide；2-(chloromethyl)-1-benzothiophene 1,1-dioxide
• CAS: 101724-26-9
• 化学式: C₉H₇ClO₂S
• 分子量: 214.672
• InChiKey: RSOLGIRVKSWATQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 2-Chlormethyl-benzothiophen-dioxid-(1,1) 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以65%的产率得到N-(benzothiophenesulfone-2-methoxy)succinimide
  参考文献：
  名称：

  The 1,1-Dioxobenzo[b]thiophene-2-ylmethyloxycarbonyl (Bsmoc) Amino-Protecting Group

  摘要：

  Full details are presented for use of the Bsmoc amino-protecting group for both solid phase and rapid continuous solution syntheses. Application to the latter methodology represents a significant improvement over the corresponding Fmoc-based method for rapid solution synthesis due to the opportunity to use water or saturated sodium-chloride solution rather than an acidic phosphate buffer to remove all byproducts, with consequent cleaner phase separation and higher yields of the growing peptide. Comparison of the Bsmoc and Bspoc functions showed that the former, because of steric hindrance, does not suffer from the competitive or premature deblocking observed with the Bspoc system. Because of its incorporation of a styrene chromophore, resin loading of Bsmoc amino acids could be followed as has previously been shown for the Fmoc analogues. Applications of Bsmoc chemistry to peptide sequences incorporating the base sensitive Asp-Gly unit gave less contamination due to aminosuccinimide formation than comparable syntheses involving standard Fmoc chemistry because a weaker or less concentrated base could be used in the deblocking step. Experimental details are presented for building up peptides in solution via the continuous methodology. Deblockings involved the use of insoluble piperazino silica as well as the polyamine TAEA which simplified aqueous separation of the growing, but nonisolated peptide product, from excess acylating agent and other side products formed in the deblocking process. By the appropriate choice of base, one can act selectively at either site of a molecule which incorporates both beta-elimination and Michael acceptor sites as protective units (Bsmoc vs Fm and Fmoc vs Bsm).

  DOI：

  10.1021/jo982140l

文献信息

• Thermally-cleavable protecting and linker groups
  申请人：EVONETIX LTD

  公开号：US11161869B2

  公开（公告）日：2021-11-02

  The present invention relates to chemical linkers and protecting groups, compounds and compositions containing the chemical linkers or protecting groups, and intermediates and processes that can be used to prepare them. The chemical linkers and protecting groups are based on pyrrolidine and piperidine activating groups, which undergo intramolecular cyclisation upon heating with release of carbon dioxide, thereby releasing the organic compound from a substrate. In particular, those chemical linkers and protecting groups are useful in the solid phase synthesis of oligonucleotides according to the following representative schemes.

  本发明涉及化学连接体和保护基团、含有化学连接体或保护基团的化合物和组合物，以及可用于制备它们的中间体和工艺。这些化学连接剂和保护基团以吡咯烷和哌啶活化基团为基础，在加热并释放二氧化碳时，这些基团会发生分子内旋转，从而将有机化合物从底物中释放出来。这些化学连接剂和保护基团尤其适用于根据以下代表性方案进行寡核苷酸的固相合成。
• BICYCLISCHE SULFONE, VERFAHREN ZU IHRER HERSTELLUNG UND DIESE ENTHALTENDE ARZNEIMITTEL
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0601002A1

  公开（公告）日：1994-06-15
• OLIGONUCLEOTIDE AND NUCLEIC ACID SYNTHESIS
  申请人：EVONETIX LTD

  公开号：US20210047361A1

  公开（公告）日：2021-02-18

  The present invention relates to methods for the high fidelity synthesis of oligonucleotides and polynucleotides on a solid surface. In particular, the invention relates to methods of synthesising oligonucleotides, polynucleotides, and doublestranded polynucleotides/nucleic acids, such as DNA and XNA, wherein the process comprises thermally controlled deprotection steps at the 5′-OH of previously coupled nucleosides or nucleotides at selected sites on the surface of the substrate.
• THERMALLY-CLEAVABLE PROTECTING AND LINKER GROUPS
  申请人：EVONETIX LTD

  公开号：US20210107934A1

  公开（公告）日：2021-04-15

  The present invention relates to chemical linkers and protecting groups, compounds and compositions containing the chemical linkers or protecting groups, and intermediates and processes that can be used to prepare them. The chemical linkers and protecting groups are based on pyrrolidine and piperidine activating groups, which undergo intramolecular cyclisation upon heating with release of carbon dioxide, thereby releasing the organic compound from a substrate. In particular, those chemical linkers and protecting groups are useful in the solid phase synthesis of oligonucleotides according to the following representative schemes.
• US3946038A
  申请人：——

  公开号：US3946038A

  公开（公告）日：1976-03-23