6-benzyloxyhexyl 2-O-acetyl-3,4-O-isopropylidene-6-deoxy-6-oxo-β-D-galactopyranoside | 1448550-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-benzyloxyhexyl 2-O-acetyl-3,4-O-isopropylidene-6-deoxy-6-oxo-β-D-galactopyranoside
• CAS: 1448550-04-6
• 化学式: C₂₄H₃₄O₈
• 分子量: 450.529
• InChiKey: NEFJETIZCUWINB-BMXMUORJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  32.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6-benzyloxyhexyl 2-O-acetyl-3,4-O-isopropylidene-6-deoxy-6-oxo-β-D-galactopyranoside 、 methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-(benzenesulfonyl)-6-[(1R,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-{(R)-hydroxy-[6-(6-benzyloxyhexyl 2-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosidyl)]methyl}-D-erythro-L-mannonononate 、 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-{(S)-hydroxy-[6-(6-benzyloxyhexyl 2-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosidyl)]methyl}-D-erythro-L-mannonononate
  参考文献：
  名称：

  Synthesis of Neu5Ac-α-C-galactopyranosyl-functionalized magnetic nanoparticles via click chemistry

  摘要：

  A new type of glyco-nanoparticle has been accomplished through Cu(I)-catalyzed 1,3-dipolar cycloaddition of 6-azidohexyl Neu5Ac-alpha-C-galactoside and N-propargyl derivative, which was attached on a silica-wrapping magnetic nanoparticle. Neu5Ac-alpha-C-galactoside was stereo-selectively synthesized in 11 steps from isopropyl thiogalactopyranoside and per-acetylated Neu5Ac phenylsulfone using samarium-mediated reductive desulfonylation as the key step. Magnetic nanoparticles were prepared with one-step hydrothermal method and a subsequent coating with (N,N'-di-propargyl-3-aminopropyol) triethoxysilane derivative. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.086
• 作为产物：
  描述：

  isopropyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 在 四丁基氟化铵 、 sodium methylate 、 对甲苯磺酸 、 三乙胺 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 38.67h， 生成 6-benzyloxyhexyl 2-O-acetyl-3,4-O-isopropylidene-6-deoxy-6-oxo-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Neu5Ac-α-C-galactopyranosyl-functionalized magnetic nanoparticles via click chemistry

  摘要：

  A new type of glyco-nanoparticle has been accomplished through Cu(I)-catalyzed 1,3-dipolar cycloaddition of 6-azidohexyl Neu5Ac-alpha-C-galactoside and N-propargyl derivative, which was attached on a silica-wrapping magnetic nanoparticle. Neu5Ac-alpha-C-galactoside was stereo-selectively synthesized in 11 steps from isopropyl thiogalactopyranoside and per-acetylated Neu5Ac phenylsulfone using samarium-mediated reductive desulfonylation as the key step. Magnetic nanoparticles were prepared with one-step hydrothermal method and a subsequent coating with (N,N'-di-propargyl-3-aminopropyol) triethoxysilane derivative. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.086