2-pyridyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside | 74352-37-7

• 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: 2-pyridyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
• 英文别名: 2-Pyridyl 2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-pyridin-2-ylsulfanyloxan-2-yl]methyl acetate
• CAS: 74352-37-7
• 化学式: C₁₉H₂₃NO₉S
• 分子量: 441.459
• InChiKey: MGGZRMLMASJEHA-FTWQHDNSSA-N

物化性质

• 熔点：
  127-180 °C
• 沸点：
  530.0±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-pyridyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 在 sodium methylate 、 mercury(II) nitrate 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 1,6-脱水-β-D-葡萄糖
  参考文献：
  名称：

  Chemistry of the glycosidic linkage. Exceptionally fast and efficient formation of glycosides by remote activation

  摘要：

  DOI：

  10.1016/s0008-6215(00)84882-x
• 作为产物：
  描述：

  2,2'-二硫二吡啶 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 rongalite 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 以65%的产率得到2-pyridyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Useful approach to the synthesis of aryl thio- and selenoglycosides in the presence of rongalite

  摘要：

  A simple, mild, and cost effective methodology has been developed for the synthesis of aryl thio-and selenoglycosides from glycosyl halides and diaryl dichalcogenides. Diaryl dichalcogenides undergo reductive cleavage in the presence of rongalite (HOCH2SO2Na) to generate a chalcogenide anion in situ followed by reaction with glycosyl halides to furnish the corresponding aryl thio- and selenoglycosides in excellent yields. Using this protocol, synthesis of 4-methyl-7-thioumbelliferyl-β-D-cellobioside (MUS-CB), a fluorescent non-hydrolyzable substrate analogue for cellulases has been achieved.

  DOI：

  10.1016/j.carres.2014.07.011

文献信息

• Electrochemical nickel-catalyzed Migita cross-coupling of 1-thiosugars with aryl, alkenyl and alkynyl bromides
  作者：Mingxiang Zhu、Mouad Alami、Samir Messaoudi

  DOI：10.1039/d0cc01126f

  日期：——

  Here we report a simple route towards the synthesis of thioglycosides, in which electrochemical cross-coupling is used to form a S-C glycosidic bond from protected and unprotected thiosugars with functionalized aryl bromides under base free conditions. The reaction manifold that we report here demonstrates the power of electrochemistry to access highly complex glycosides under mild conditions.

  在这里，我们报告了一种简单的合成硫糖苷的方法，其中电化学交叉偶联用于在无碱条件下由受保护和未受保护的硫糖与功能化的芳基溴化物形成SC糖苷键。我们在此报告的反应歧管证明了在温和条件下电化学作用可获取高度复杂的糖苷的能力。
• Stereoselective synthesis of α-linked saccharides by use of per O-benzylated 2-pyridyl 1-thio hexopyranosides as glycosyl donors and methyl iodide as an activator
  作者：Hari Babu Mereyala、G Venugopal Reddy

  DOI：10.1016/s0040-4020(01)86571-6

  日期：1991.8

  D-manno-(3) and L-rhamno-(4) configurations have been efficiently coupled with diverse sugar alcohols (6,8–11) on activation by methyl iodide to obtain the α-linked disaccharides (7,12–19). Coupling of donor 1 with the disaccharide acceptor 20 and the disaccharide donor 5 with 8 to obtain α-linked trisaccharides 21 and 22 is also described. A possible mechanism for the α-selectivity is also discussed

  描述了一种新的，实用的，立体选择性糖苷化方法，其中每个D-葡萄糖-（1），D-半乳糖-（2），D-甘露聚糖-（- ）的O-苄基化2-吡啶基1-硫代-α/β-己吡喃糖基3）和L-鼠李糖（4）构型已通过甲基碘活化与各种糖醇（6,8-11）有效偶联，获得了α-连接的二糖（7,12-19）。供体1与二糖受体20的偶联，以及二糖供体5与8的偶联，以获得α-连接的三糖21和22也进行了描述。还讨论了α选择性的可能机理。
• Directed, iterative, stereoselective synthesis of oligosaccharides by use of suitably 2--substituted 2-pyridyl 1-thioglycopyranosides on activation by methyl iodide
  作者：Hari Babu Mereyala、G Venugopal Reddy

  DOI：10.1016/s0040-4020(01)91035-x

  日期：1991.11

  The title synthesis is described by the proven methyl iodide activation procedure to obtain the α-linked oligosaccharides.

  通过已证明的甲基碘活化程序来描述标题合成以获得α-连接的寡糖。
• Stereoselective Syntheses of 1,2-trans<i>p</i>-MePh and 2-Pyridyl 1-Thioglycosides Catalyzed by Zirconium(IV) Chloride
  作者：Yili Ding

  DOI：10.1080/00397919908085987

  日期：1999.10

  1-Thioglycosides including per-O-acetyl p-MePh and 2-pyridyl 1-thioglycosides were chemically synthesized with high complete stereoselectivity by using ZrCl4 as catalyst.
• A New Approach to the Synthesis of Benzothiazole, Benzoxazole, and Pyridine Nucleosides as Potential Antitumor Agents
  作者：Ahmed I. Khodair、Najim A. Al-Masoudi、Jean-Pierre Gesson

  DOI：10.1081/ncn-120026407

  日期：2003.11

  A modified nitrogen and sulfur glycosylation reaction involving benzothiazole benzoxazole and pyridine nucleoside bases with furanose and pyranose sugars are described. Conformational analysis has been studied by homo- and hetero-nuclear two-dimensional NMR methods (2D DFQ-COSY, HMQC and HMBC). The N and S sites of glycosylation were determined from the H-1, C-13 hetero-nuclear multiple-quantum coherence (HMQC) experiments. All the deprotected nucleosides were tested for their potential antitumor activity.