N-succinyl-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)sulfenamide | 1318852-98-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-succinyl-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)sulfenamide
• 英文别名: 2,3,4,6-tetra-O-acetyl-1-S-(pyrrolidine-2,5-dione)-1-thio-β-D-glucopyranoside
• CAS: 1318852-98-0
• 化学式: C₁₈H₂₃NO₁₁S
• 分子量: 461.447
• InChiKey: NRNNEBPROPDUCJ-CUWKQTPXSA-N

物化性质

• 熔点：
  197-199 °C
• 沸点：
  544.4±60.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.13
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  151.81
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N-succinyl-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)sulfenamide 、 2,3,4,6-四-O-乙酰基-1-硫代-BETA-D-吡喃半乳糖 以 二氯甲烷 为溶剂， 反应 0.33h， 以85%的产率得到S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-S'-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)disulfide
  参考文献：
  名称：

  Glycosylation via mixed disulfide formation using glycosylthio-phthalimides and -succinimides as glycosylsulfenyl-transfer reagents

  摘要：

  The silver salts of tetra-O-acetyl alpha- or -beta-D-glycopyranosyl thiols 1a-4a react smoothly with N-bromophthalimide and N-bromosuccinimide to furnish glycosylthio-phthalimide (1b-4b) and -succinimide (1c-3c) derivatives. Reactions of these reagents with aliphatic, aromatic, and glycosyl thiols as well as with cysteine and glutathione result in the formation of glycosylated mixed disulfides under mild conditions and in good yields. The S-glycosyl-N-acylsulfenamides described here represent novel, convenient glycosylsulfenyl-transfer reagents in effecting glycosylation of various thiols, including sugars, amino acids and peptides, through disulfide formation and can, therefore, be useful in controlled glycosylation of proteins as well. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.020
• 作为产物：
  描述：

  N-溴代丁二酰亚胺(NBS) 、 1-硫代-b-D-葡萄糖四乙酸酯 在 silver(I) acetate 作用下， 以 乙酸乙酯 为溶剂， 反应 0.84h， 以65%的产率得到N-succinyl-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)sulfenamide
  参考文献：
  名称：

  Glycosylation via mixed disulfide formation using glycosylthio-phthalimides and -succinimides as glycosylsulfenyl-transfer reagents

  摘要：

  The silver salts of tetra-O-acetyl alpha- or -beta-D-glycopyranosyl thiols 1a-4a react smoothly with N-bromophthalimide and N-bromosuccinimide to furnish glycosylthio-phthalimide (1b-4b) and -succinimide (1c-3c) derivatives. Reactions of these reagents with aliphatic, aromatic, and glycosyl thiols as well as with cysteine and glutathione result in the formation of glycosylated mixed disulfides under mild conditions and in good yields. The S-glycosyl-N-acylsulfenamides described here represent novel, convenient glycosylsulfenyl-transfer reagents in effecting glycosylation of various thiols, including sugars, amino acids and peptides, through disulfide formation and can, therefore, be useful in controlled glycosylation of proteins as well. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.020

文献信息

• Stereoretentive C(<i>sp</i>³)–S Cross-Coupling
  作者：Feng Zhu、Eric Miller、Shuo-qing Zhang、Duk Yi、Sloane O’Neill、Xin Hong、Maciej A. Walczak

  DOI：10.1021/jacs.8b11211

  日期：2018.12.26

  We report a stereoretentive cross-coupling reaction of configurationally stable nucleophiles with disulfide and N-sulfenylsuccinimide donors promoted by Cu(I). We demonstrate the utility of this method in the synthesis of thioglycosides derived from simple alkyl and aryl thiols, thioglycosides, and in the glycodiversification of cysteine residues in peptides. These reactions operate well with carbohydrate

  我们报告了由 Cu(I) 促进的构型稳定的亲核试剂与二硫化物和 N-亚磺酰基琥珀酰亚胺供体的立体保持交叉偶联反应。我们证明了该方法在合成衍生自简单烷基和芳基硫醇、硫糖苷的硫糖苷以及肽中半胱氨酸残基的糖多样化中的实用性。在标准化条件下，这些反应在含有常见保护基团的碳水化合物底物和具有游离羟基和仲酰胺官能团的试剂上运行良好。竞争实验与计算 DFT 研究相结合确定了假定的异头中间体是一种有机铜物种，由于其寿命短，其构型稳定且抗差向异构化。随后从 Cu(III) 中间体的还原消除是快速和立体保持的。总之，糖基交叉偶联非常适合在脂肪族碳硫键的高度受控安装下的后期糖多样化和生物共轭。
• A Method for the Synthesis of Thioindoles through Copper-Catalyzed C–S Bond Coupling Reaction
  作者：Jie Huang、Jin-Quan Li、Xin-Yue Cui、Yi-Han Qin、Shi-Jie Ma、Zi-An An、Wen-Wu Sun、Bin Wu

  DOI：10.1021/acs.joc.3c02008

  日期：2024.1.5

  We herein report the copper-catalyzed C–S bond coupling reaction of indoles with N-thiosuccinimides, resulting in moderate to excellent yields of mono- and bis-sulfenylated compounds such as arylthioindoles, alkylthioindoles, selenylated indoles, and cysteine-substituted indoles. Thioarylation and thioglycosylation at the C2 position of indole alkaloids in the Radix Isatidis were achieved via structural

  我们在此报道了铜催化吲哚与N-硫代琥珀酰亚胺的C-S键偶联反应，产生中等至优异的单磺酰化和双磺酰化化合物，如芳硫基吲哚、烷硫基吲哚、硒化吲哚和半胱氨酸取代的吲哚。板蓝根中吲哚生物碱C2位的硫代芳基化和硫代糖基化是通过结构修饰实现的。靛蓝靛甙III和IV的首次全合成已成功进行。原位产生的亲电子次磺基溴在催化循环中发挥重要作用。