6-(phenylmethoxy)-1-hexyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside | 93619-74-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-(phenylmethoxy)-1-hexyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
• 英文别名: 6-benzyloxyhexyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
• CAS: 93619-74-0
• 化学式: C₂₇H₃₈O₁₁
• 分子量: 538.592
• InChiKey: NYELVWVAGAGHOU-LXSUACKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  38.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  132.89
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  6-(phenylmethoxy)-1-hexyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium methylate 、 对甲苯磺酸 作用下， 反应 48.0h， 生成 6-(phenylmethoxy)-1-hexyl 2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Solution- and Solid-Phase Synthesis of Inhibitors of H. pylori Attachment and E-Selectin-Mediated Leukocyte Adhesion

  摘要：

  Chemical and enzymatic methods have been developed for the synthesis of the oligosaccharides NeuAc alpha 2-->3Gal beta 1 -->4GlcNAc beta 1-->3Gal and NeuAc alpha 2-->3Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc beta 1-->3Gal as inhibitors for H. pylori and E-selectin, respectively. Gal, NeuAc, and Fuc were incorporated sequentially into the synthetic primer GlcNAc beta 1-->3Gal beta OEt by the corresponding glycosyltransferases to give both the tetrasaccharide and the pentasaccharide. This solution-phase strategy was then extended to the solid-phase synthesis of the tetrasaccharide. A disaccharide primer was first attached to controlled pore glass via a spacer group containing an ester bond, followed by enzymatic incorporation of Gal and NeuAc. Two to three equivalents of sugar nucleotides were used in the enzymatic glycosylationl and the conversion for each step was found to be > 98% as indicated in the analysis of products released by treatment with hydrazine.

  DOI：

  10.1021/ja00104a011
• 作为产物：
  描述：

  2,2,2-三氯乙酰胺苄酯 在 lithium aluminium tetrahydride 、 三氟甲磺酸 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 6-(phenylmethoxy)-1-hexyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Solution- and Solid-Phase Synthesis of Inhibitors of H. pylori Attachment and E-Selectin-Mediated Leukocyte Adhesion

  摘要：

  Chemical and enzymatic methods have been developed for the synthesis of the oligosaccharides NeuAc alpha 2-->3Gal beta 1 -->4GlcNAc beta 1-->3Gal and NeuAc alpha 2-->3Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc beta 1-->3Gal as inhibitors for H. pylori and E-selectin, respectively. Gal, NeuAc, and Fuc were incorporated sequentially into the synthetic primer GlcNAc beta 1-->3Gal beta OEt by the corresponding glycosyltransferases to give both the tetrasaccharide and the pentasaccharide. This solution-phase strategy was then extended to the solid-phase synthesis of the tetrasaccharide. A disaccharide primer was first attached to controlled pore glass via a spacer group containing an ester bond, followed by enzymatic incorporation of Gal and NeuAc. Two to three equivalents of sugar nucleotides were used in the enzymatic glycosylationl and the conversion for each step was found to be > 98% as indicated in the analysis of products released by treatment with hydrazine.

  DOI：

  10.1021/ja00104a011

文献信息

• Synthesis of Neu5Ac-α-C-galactopyranosyl-functionalized magnetic nanoparticles via click chemistry
  作者：Chaoli Zhang、Xing Ma、Yuguo Du

  DOI：10.1016/j.tet.2013.06.086

  日期：2013.9

  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.
• Synthesis of galactosyl phosphate diester derivatives of nucleosides
  作者：Tian-Wei Ma、Ji-Mei Min、Li-He Zhang

  DOI：10.1016/0008-6215(94)80046-4

  日期：1994.5
• Collins, Peter M.; Eder, Hansjoerg, Journal of the Chemical Society. Perkin transactions I, 1984, # 7, p. 1525 - 1530
  作者：Collins, Peter M.、Eder, Hansjoerg

  DOI：——

  日期：——