phenyl 4-O-acetyl-3-azido-1-thio-2,3,6-trideoxy-α-L-arabino-hexopyranoside | 283170-19-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl 4-O-acetyl-3-azido-1-thio-2,3,6-trideoxy-α-L-arabino-hexopyranoside
• 英文别名: [(2S,3R,4S,6S)-4-azido-2-methyl-6-phenylsulfanyloxan-3-yl] acetate
• CAS: 283170-19-4
• 化学式: C₁₄H₁₇N₃O₃S
• 分子量: 307.373
• InChiKey: NMLSBVHAEGMGJS-HBEIAFGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 4-O-acetyl-3-azido-1-thio-2,3,6-trideoxy-α-L-arabino-hexopyranoside 在 吡啶 、 lithium hydroxide 、 2,6-二叔丁基-4-甲基吡啶 、 18-冠醚-6 、 三氟甲磺酸酐 、 4 A molecular sieve 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 7.25h， 生成 phenyl (3-azido-2,3-dideoxy-α-L-fucopyranosyl)-(1-4)-3-azido-2,3-dideoxy-1-thio-α-L-fucopyranoside
  参考文献：
  名称：

  Design of an Oligosaccharide Scaffold That Binds in the Minor Groove of DNA

  摘要：

  Many biological recognition events involve extensive interactions between macromolecules. Strategies to design compounds that mimic large peptides or other elements of secondary structure could be useful for blocking interactions between large surfaces. In this paper, the use of oligosaccharides as scaffolds for the design of peptidomimetics is addressed. A functionalized oligosaccharide modeled after a basic region peptide helix has been designed and synthesized. This oligosaccharide binds to duplex DNA with micromolar affinity. The mode of binding has been established by 2D NMR, and shows that the oligosaccharide binds DNA in the minor groove with one surface of the oligosaccharide contacting the floor of the DNA.

  DOI：

  10.1021/ja992513f
• 作为产物：
  描述：

  2-deoxy-3-azido-4-O-acetyl-L-rhamnopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.66h， 生成 phenyl 4-O-acetyl-3-azido-1-thio-2,3,6-trideoxy-α-L-arabino-hexopyranoside
  参考文献：
  名称：

  Design of an Oligosaccharide Scaffold That Binds in the Minor Groove of DNA

  摘要：

  Many biological recognition events involve extensive interactions between macromolecules. Strategies to design compounds that mimic large peptides or other elements of secondary structure could be useful for blocking interactions between large surfaces. In this paper, the use of oligosaccharides as scaffolds for the design of peptidomimetics is addressed. A functionalized oligosaccharide modeled after a basic region peptide helix has been designed and synthesized. This oligosaccharide binds to duplex DNA with micromolar affinity. The mode of binding has been established by 2D NMR, and shows that the oligosaccharide binds DNA in the minor groove with one surface of the oligosaccharide contacting the floor of the DNA.

  DOI：

  10.1021/ja992513f

文献信息

• General Method for the Synthesis of α- or β-Deoxyaminoglycosides Bearing Basic Nitrogen
  作者：Kevin M. Hoang、Nicholas R. Lees、Seth B. Herzon

  DOI：10.1021/jacs.0c11262

  日期：2021.2.24

  often produced. Herein, we present a method for the synthesis of α- or β- 2,3,6-trideoxy-3-amino- and 2,4,6-trideoxy-4-amino O-glycosides from a common precursor. Our strategy proceeds by the reductive lithiation of thiophenyl glycoside donors and trapping of the resulting anomeric anions with 2-methyltetrahydropyranyl peroxides. We apply this strategy to the synthesis of α- and β-forosamine, pyrrolosamine

  由于胺与路易斯酸促进剂的竞争性配位，使用传统的路易斯酸促进途径引入带有碱性氮的糖苷具有挑战性。此外，由于许多氨基糖苷缺少 C2 取代基，因此经常产生O-糖苷的非对映异构混合物。在此，我们提出了一种合成 α- 或 β- 2,3,6-trideoxy-3-amino- 和 2,4,6-trideoxy-4-amino O 的方法-来自常见前体的糖苷。我们的策略通过苯硫基糖苷供体的还原锂化和用 2-甲基四氢吡喃过氧化物捕获产生的异头阴离子进行。我们将此策略应用于使用初级和次级过氧化物作为亲电试剂合成 α- 和 β-forosamine、吡咯胺、acosamine 和 ristosamine 衍生物。以 60-96% 的产率和 >50:1 的选择性获得 α-连接的产物。β-连接产物的产率为 45-94%，立体选择性为 1.7->50:1。与带有赤道胺取代基的供体相反，带有轴向胺取代基的供体在低温下
• A Practical Method for the Stereoselective Generation of β-2-Deoxy Glycosyl Phosphates
  作者：Markus Oberthür、Catherine Leimkuhler、Daniel Kahne

  DOI：10.1021/ol049187f

  日期：2004.8.1

  beta-2-Deoxy sugar nucleotides are substrates used by a variety of glycosyltransferases (Gtfs). We have developed a chemical route to synthesize beta-2-deoxy sugar phosphates that starts from a-glycosyl chlorides. Our approach reliably provides access to a range of NDP beta-2-deoxy sugars essential for studying glycosyltransferases involved in the synthesis of biologically active natural products.