2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl iodide | 793696-64-7

• 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: 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl iodide
• 英文别名: 2,3,4-O-acetyl-α-L-rhamnopyranosyl iodide；[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-iodo-2-methyloxan-3-yl] acetate
• CAS: 793696-64-7
• 化学式: C₁₂H₁₇IO₇
• 分子量: 400.167
• InChiKey: VWEBALSINHQLCC-YTYCZEAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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-α-L-rhamnopyranosyl iodide 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 3,5-dimethoxyphenyl 2,3,4-tri-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Visible-light-promoted 3,5-dimethoxyphenyl glycoside activation and glycosylation

  摘要：

  一种以3,5-二甲氧基苯基糖苷为供体的可见光促进糖基化方法被开发出来。

  DOI：

  10.1039/d1cc04473g
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 在 碘 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl 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。
• The Cephalostatins. 21. Synthesis of Bis-steroidal Pyrazine Rhamnosides
  作者：George R. Pettit、Ricardo F. Mendonça、John C. Knight、Robin K. Pettit

  DOI：10.1021/np200411p

  日期：2011.9.23

  The synthesis of bis-steroidal pyrazines derived from 3-oxo-11,21-dihydroxypregna-4,17(20)-diene (4) and glycosylation of a D-ring side chain with α-l-rhamnose have been summarized. Rearrangement of steroidal pyrazine 10 to 14 was found to occur with boron triflouride etherate. Glycosylation of pyrazine 10 using 2,3,4-tri-O-acetyl-α-l-rhamnose iodide led to 1,2-orthoester-α-l-rhamnose pyrazine 17b

  已经总结了衍生自 3-oxo-11,21-dihydroxypregna-4,17(20)-diene ( 4 )的双甾体吡嗪的合成和 D 环侧链与 α- 1-鼠李糖的糖基化。发现甾体吡嗪10至14 的重排与三氟化硼醚合物一起发生。使用 2,3,4-三-O-乙酰基-α- 1-鼠李糖碘化物对吡嗪10进行糖基化生成 1,2-原酸酯-α- 1-鼠李糖吡嗪17b。通过使用全甲硅烷基化的α- 1-鼠李糖碘化物作为供体，避免了原酸酯的形成。双甾体吡嗪10和鼠李糖苷17b发现21c和21c在鼠和人癌细胞系组中显着抑制癌细胞生长。吡嗪9抑制了医院病原体粪肠球菌的生长。
• Efficient synthesis of thioglycosylated kojic acid by<i>s</i>-glycosyl isothiouronium salts
  作者：Zhimeng Wu、Aijie Cao、Wenzhang Ding、Tao Zhu、Peng Shen

  DOI：10.1080/07328303.2016.1261881

  日期：2016.9.1

  In this study, 7-S-glycosides of kojic acid were designed and synthesized as mimics of its 7-O-glycosides to improve its water solubility and metabolic stability. To achieve this synthesis, a one-pot approach involving S-glycosyl isothiouronium salts generated in situ as key intermediates was developed by using 7-chloro-kojic acid as the alkylation reagent. A series of water soluble 7-S-glycosides of kojic acid, incorporating monosaccharides and disaccharides, were prepared using this protocol. Thus, this work offers a mild, convenient, and efficient approach for the synthesis of 7-S-glycosides of kojic acid in medium to good yields.[GRAPHICS].