2,3,4-tri-O-acetyl-β-L-arabinopyranosyl iodide | 14227-79-3

• 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: 2,3,4-tri-O-acetyl-β-L-arabinopyranosyl iodide
• 英文别名: tri-O-acetyl-β-L-arabinopyranosyl iodide；Tri-O-acetyl-β-L-arabinopyranosyljodid；[(3S,4S,5R,6R)-4,5-diacetyloxy-6-iodooxan-3-yl] acetate
• CAS: 14227-79-3
• 化学式: C₁₁H₁₅IO₇
• 分子量: 386.14
• InChiKey: LKVJDIPGZMVVSH-MMWGEVLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-β-L-arabinopyranosyl iodide 、 4-甲苯硫酚 以 二氯甲烷 为溶剂， 生成 p-tolyl 2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside
  参考文献：
  名称：

  Streamlined Synthesis of Per-O-acetylated Sugars, Glycosyl Iodides, or Thioglycosides from Unprotected Reducing Sugars¹

  摘要：

  Solvent-free per-O-acetylation of sugars with stoichiometric acetic anhydride and catalytic iodine proceeds in high yield (90-99%) to give exclusively pyranose products as anomeric mixtures. Without workup, subsequent anomeric substitution employing iodine in the presence of hexamethyldisilane (i.e., TMS-I generated in situ) gives the corresponding glycosyl iodides in 75-95% isolated yield. Alternatively, and without workup, further treatment with dimethyl disulfide or thiol (ethanethiol or thiocresol) gives anomerically pure thioglycosides in more than 75% overall yield.

  DOI：

  10.1021/jo048890e
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-L-arabinopyranose 在 碘 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 2,3,4-tri-O-acetyl-β-L-arabinopyranosyl iodide
  参考文献：
  名称：

  Streamlined Synthesis of Per-O-acetylated Sugars, Glycosyl Iodides, or Thioglycosides from Unprotected Reducing Sugars¹

  摘要：

  Solvent-free per-O-acetylation of sugars with stoichiometric acetic anhydride and catalytic iodine proceeds in high yield (90-99%) to give exclusively pyranose products as anomeric mixtures. Without workup, subsequent anomeric substitution employing iodine in the presence of hexamethyldisilane (i.e., TMS-I generated in situ) gives the corresponding glycosyl iodides in 75-95% isolated yield. Alternatively, and without workup, further treatment with dimethyl disulfide or thiol (ethanethiol or thiocresol) gives anomerically pure thioglycosides in more than 75% overall yield.

  DOI：

  10.1021/jo048890e

文献信息

• Synthetic Ellagic Acid Glycosides Inhibit Early Stage Adhesion of <i>Streptococcus agalactiae</i> Biofilms as Observed by Scanning Electron Microscopy
  作者：Schuyler A. Chambers、Jennifer A. Gaddy、Steven D. Townsend

  DOI：10.1002/chem.202000354

  日期：2020.8.6

  in Streptococcus agalactiae (Group B Streptococcus , GBS). Their significant impacts on biofilm formation were examined via SEM to reveal early‐stage inhibition of cellular adhesion. Additionally, the synthetic glycosides were evaluated against five of the six ESKAPE pathogens and two fungal pathogens. These studies reveal that the ellagic acid glycosides possess inhibitory effects on the growth of

  鞣花酸衍生物对多种微生物病原体具有抗菌和抗生物膜特性。由于它们的溶解性差和反应性差，因此合成、纯化和表征鞣花酸糖苷的活性具有挑战性。在这项研究中，我们合成了三种鞣花酸糖缀合物，并评估了它们在无乳链球菌（B 组链球菌）中的抗菌和抗生物膜活性。, GBS)。通过 SEM 检查它们对生物膜形成的显着影响，以揭示细胞粘附的早期抑制。此外，还针对六种 ESKAPE 病原体中的五种和两种真菌病原体对合成糖苷进行了评估。这些研究表明，鞣花酸苷对革兰氏阴性病原体的生长具有抑制作用。
• FLUORO-ACETYL DERIVATIVES OF SUGARS. III. OPTICAL ROTATION AND ATOMIC DIMENSION (CONTINUED)
  作者：D. H. Brauns

  DOI：10.1021/ja01671a019

  日期：1924.6