1,1-二杂苯[B]硫代苯甲基N-琥珀酸胺碳酸盐 | 197244-91-0

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物
• 中文名称: 1,1-二杂苯[B]硫代苯甲基N-琥珀酸胺碳酸盐
• 中文别名: (1,1-二氧苯并噻吩-2-基)甲基(2,5-二氧代吡咯烷-1-基)碳酸酯；(1,1-二氧-苯并噻吩-2-甲基)丁二酸亚胺基甲酸酯,95；(1,1-二氧-苯并噻吩-2-甲基)丁二酸亚胺基甲酸酯
• 英文名称: 1,1-dioxobenzo[b]thiophen-2-ylmethyl N-succimidyl carbonate
• 英文别名: (1,1-Dioxidobenzo[b]thiophen-2-yl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate；(1,1-dioxo-1-benzothiophen-2-yl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate
• CAS: 197244-91-0
• 化学式: C₁₄H₁₁NO₇S
• 分子量: 337.31
• InChiKey: XBVMGLSMCWWRLS-UHFFFAOYSA-N

物化性质

• 熔点：
  ~165 °C (dec.)
• 稳定性/保质期：
  避免与氧化物和水分接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• WGK Germany：
  3
• 海关编码：
  2934999090
• 安全说明：
  S22
• 储存条件：
  保存方法：存放在密闭、阴凉和干燥的地方。

反应信息

• 作为反应物：
  描述：

  1,1-二杂苯[B]硫代苯甲基N-琥珀酸胺碳酸盐 在 吡啶 、 三聚氟氰 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.25h， 生成 Bsmoc-Asp(O-t-Bu)-F
  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
• 作为产物：
  描述：

  benzothiophen-2-yllithium 在 sodium perborate 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 20.0h， 生成 1,1-二杂苯[B]硫代苯甲基N-琥珀酸胺碳酸盐
  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

• Therapeutic Monosaccharide-Based Inhibitors of Hexokinase and Glucokinase for Parasitic Diseases, Along with Methods of their Formation and Use
  申请人：University of South Carolina

  公开号：US20160145291A1

  公开（公告）日：2016-05-26

  Methods for treating a mammal that is infected by a parasitic organism are provided, along with pharmaceutical compositions and compounds. The method includes administering to the mammal the pharmaceutical composition of FIG. 1, where: R 1 , R 2 , R 3 , and R 4 comprises, independently, H, OH, NH 2 , SH, a halogen, or an organic group or a derivative thereof; X 1 is O, NH, CH 2 , or S; m is 0 or 1; X 2 comprises an organic linkage, such as CH 2 ; n is an integer from 0 to 10; and R 5 comprises an aromatic organic group.

  提供了一种治疗被寄生生物感染的人畜的方法，以及药物组合物和化合物。该方法包括向人畜投给FIG.1的药物组合物，其中：R1、R2、R3和R4独立地包括H、OH、NH2、SH、卤素或有机组分的衍生物；X1为O、NH、CH2或S；m为0或1；X2包括如CH2的有机键；n为0到10的整数；R5包括芳香族有机组分。
• Protecting‐Group‐Controlled Enzymatic Glycosylation of Oligo‐ <i>N</i> ‐Acetyllactosamine Derivatives
  作者：Ivan A. Gagarinov、Tiehai Li、Na Wei、Javier Sastre Toraño、Robert P. de Vries、Margreet A. Wolfert、Geert‐Jan Boons

  DOI：10.1002/anie.201903140

  日期：2019.7.29

  easily be converted into 6 different hexasaccharides in which the glucosamine moieties are either acetylated (GlcNAc) or modified as a free amine (GlcNH2) or Boc (GlcNHBoc). Fucosylation of the resulting compounds by a recombinant fucosyl transferase resulted in only modification of the natural GlcNAc moieties, providing access to 6 selectively mono‐ and bis‐fucosylated oligosaccharides. Conversion of

  我们描述了一种化学酶策略，该策略可以从一个化学合成的三N-乙酰乙酰乳糖胺衍生物开始提供差异岩藻糖基化和唾液酸化寡糖库。常见的前体可以轻松地转化为6种不同的六糖，其中的葡糖胺部分被乙酰化（GlcNAc）或修饰为游离胺（GlcNH 2）或Boc（GlcNHBoc）。通过重组岩藻糖基转移酶对所得化合物进行岩藻糖基化仅导致天然GlcNAc部分的修饰，从而提供了6种选择性单岩藻糖基化和双岩藻糖基化的寡糖的途径。GlcNH 2的转化或将GlcNHBoc部分插入天然GlcNAc中，然后通过唾液酸转移酶进行唾液酸化，得到12种不同的岩藻糖基化和唾液酸化化合物。寡糖以微阵列形式印刷，并由几种聚糖结合蛋白探测，表明岩藻糖基化的复杂模式可以调节聚糖识别。
• The 1,1-Dioxobenzo[<i>b</i>]thiophene-2-ylmethyloxycarbonyl (Bsmoc) Amino-Protecting Group
  作者：Louis A. Carpino、Mohamed Ismail、George A. Truran、E. M. E. Mansour、Shin Iguchi、Dumitru Ionescu、Ayman El-Faham、Christoph Riemer、Ralf Warrass

  DOI：10.1021/jo982140l

  日期：1999.6.1

  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).