methyl 2,3,4-tri-O-benzyl-3-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-β-D-galactopyranoside | 192223-18-0

• 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: methyl 2,3,4-tri-O-benzyl-3-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-β-D-galactopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-5)]Araf(a1-3)[Bz(-2)][Bz(-4)][Bz(-6)]b-Gal1Me；[(2R,3S,4S,5R,6R)-3,5-dibenzoyloxy-4-[(2S,3R,4S,5S)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)oxolan-2-yl]oxy-6-methoxyoxan-2-yl]methyl benzoate
• CAS: 192223-18-0
• 化学式: C₅₄H₄₆O₁₆
• 分子量: 950.95
• InChiKey: AEQVAQBEHQYNPL-HJHKSDEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  70
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  195
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-3-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-β-D-galactopyranoside 在 1,1-二氯甲醚 、 zinc(II) chloride 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以68%的产率得到2,3,4-tri-O-benzyl-3-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-β-D-galactopyranosyl chloride
  参考文献：
  名称：

  Synthesis of a Trisaccharide Repeating Unit Related to Arabinogalactan-Protein (AGP) Polysaccharides¹

  摘要：

  Starting from L-arabinose and methyl beta-D-galactopyranoside, methyl 2,3,4-tri-O-benzyl-6-O-[2,4,6-tri-O-benzoyl-3-O-(2,3,5 -tri-O-benzoyl-alpha-L-arabinofuranosyl)-beta-D -galactopyranosyl]-beta-D-galactopyranoside 10 has been synthesized. Removal of protecting groups gave the methyl glycoside 12 of a trisaccharide representative of a repeating unit of arabinogalactan (AGP) polysaccharides.

  DOI：

  10.1080/07328309708007326
• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 吡啶 、 2,4,6-三甲基吡啶 、 二丁醚 、 silver trifluoromethanesulfonate 、 四丁基碘化铵 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成 methyl 2,3,4-tri-O-benzyl-3-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a Trisaccharide Repeating Unit Related to Arabinogalactan-Protein (AGP) Polysaccharides¹

  摘要：

  Starting from L-arabinose and methyl beta-D-galactopyranoside, methyl 2,3,4-tri-O-benzyl-6-O-[2,4,6-tri-O-benzoyl-3-O-(2,3,5 -tri-O-benzoyl-alpha-L-arabinofuranosyl)-beta-D -galactopyranosyl]-beta-D-galactopyranoside 10 has been synthesized. Removal of protecting groups gave the methyl glycoside 12 of a trisaccharide representative of a repeating unit of arabinogalactan (AGP) polysaccharides.

  DOI：

  10.1080/07328309708007326

文献信息

• Synthesis of a Trisaccharide Repeating Unit Related to Arabinogalactan-Protein (AGP) Polysaccharides¹
  作者：Jean-François Valdor、William Mackie

  DOI：10.1080/07328309708007326

  日期：1997.5

  Starting from L-arabinose and methyl beta-D-galactopyranoside, methyl 2,3,4-tri-O-benzyl-6-O-[2,4,6-tri-O-benzoyl-3-O-(2,3,5 -tri-O-benzoyl-alpha-L-arabinofuranosyl)-beta-D -galactopyranosyl]-beta-D-galactopyranoside 10 has been synthesized. Removal of protecting groups gave the methyl glycoside 12 of a trisaccharide representative of a repeating unit of arabinogalactan (AGP) polysaccharides.