ω-acetylthiopentyl 4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)- | 349139-17-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ω-acetylthiopentyl 4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-(5-acetylsulfanylpentoxy)-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 349139-17-9
• 化学式: C₃₃H₄₈O₁₉S
• 分子量: 780.799
• InChiKey: GDQXQBSHNYWLHZ-LZWHNZSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  53
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  263
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  、 ω-acetylthiopentyl 4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)- 在 sodium methylate 、 吡啶 、 乙酸酐 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  A carbosilane dendrimer and a silacyclopentadiene analog carrying peripheral lactoses as drug-delivery systems

  摘要：

  A carbosilane dendrimer (4a) and its silacyclopentadiene analog (4b), both functionalized with lactoses, were tested for their abilities to act as drug-delivery systems. The critical micelle concentrations of 4a and 4b were measured using the drop-volume method in water and were 1.7 and 2.9 mu M, respectively, suggesting that they could act as aggregates of glycoclusters. The amounts of the hydrophobic dye Orange OT loaded onto aqueous micelles of 4a and 4b and the stabilities of the dye/micelle complexes were determined by extracting the dyes from the complexes into chloroform. The particle sizes were measured for the loaded micelles by dynamic light scattering. Transfer of the dye from the micelles to peanut agglutinin was observed by fluorescence microscopy. Given the abilities of micelles of 4a and 4b to bind and release Orange OT, these glycocluster micelles may find use as drug-delivery systems. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.034
• 作为产物：
  描述：

  硫代乙酸 、 Peracetyl pent-4-enyl β-D-lactoside 在 偶氮二异丁腈 作用下， 以 1,4-二氧六环 为溶剂， 以100%的产率得到ω-acetylthiopentyl 4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-
  参考文献：
  名称：

  An alternative route for the construction of carbosilane dendrimers uniformly functionalized with lactose or sialyllactose moieties

  摘要：

  A new approach for the formation of an acetylthio linkage on aglycon by means of a radical addition of thioacetic acid into the C-C double bond of the aglycon was examined. An introduction of a carbohydrate moiety into carbosilane dendrimers was demonstrated using a one-pot coupling reaction in MeOH-DMF in the presence of NaOMe via removal of an acetyl group of the acetylthio linkage in the saccharide moieties, producing a thiolate anion and a nucleophilic replacement of the thiolate to dendric alkyl bromide to form carbosilane dendrimers uniformly bearing lactose or sialyllactose moieties through thioether linkages in high yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00422-1

文献信息

• Syntheses and biological evaluations of carbosilane dendrimers uniformly functionalized with sialyl α(2→3) lactose moieties as inhibitors for human influenza viruses
  作者：Hiroyuki Oka、Tomotsune Onaga、Tetsuo Koyama、Chao-Tan Guo、Yasuo Suzuki、Yasuaki Esumi、Ken Hatano、Daiyo Terunuma、Koji Matsuoka

  DOI：10.1016/j.bmc.2009.06.035

  日期：2009.8

  A series of carbosilane dendrimers uniformly functionalized with sialyl lactose moieties (Neu5Ac alpha 2 -> 3-Gal beta 1 -> 4Glc) was systematically synthesized, and biological evaluations for anti-influenza virus activity using the glycodendrimers were performed. The results suggested that the glycodendrimers had unique biological activities depending on the form of their core frame, and Dumbbell(1)6-amide type glycoden-drimer 7 showed particularly strong inhibitory activities against human influenza viruses [A/PR/8/34 (H1N1) and A/Aichi/2/68 (H3N2)]. The results suggested that the structure-activity relationship (SAR) on the glycolibrary against various influenza viruses was observed, and dumbbell-shaped dendrimers as supporting carbohydrate moieties were found to be the most suitable core scaffolds in this study. (C) 2009 Elsevier Ltd. All rights reserved.
• Fluorescence quenching detection of peanut agglutinin based on photoluminescent silole-core carbosilane dendrimer peripherally functionalized with lactose
  作者：Ken Hatano、Hitoshi Saeki、Hiroo Yokota、Hiroaki Aizawa、Tetsuo Koyama、Koji Matsuoka、Daiyo Terunuma

  DOI：10.1016/j.tetlet.2009.07.153

  日期：2009.10

  A glycocluster peripherally functionalized with a lactose (Lac: Gal beta 1 -> 4Glc beta 1-) derivative possessing a silole moiety as a luminophore was synthesized. The photoluminescence spectrum of the glycocluster showed extremely strong emission at 474 nm and the absolute quantum yield was estimated to be 92% in distilled water. The emission intensity was decreased by increasing the amount of peanut agglutinin (PNA), a lactose-binding lectin, and plots of the relative fluorescence intensity revealed a decline of 95% in emission intensity. Fluorescence quenching of the glycocluster upon mixing with PNA could be easily observed by the naked eye under UV irradiation, whereas no distinct change in fluorescence properties of the glycocluster was observed when wheat germ agglutinin (WGA) was employed. (C) 2009 Elsevier Ltd. All rights reserved.