p-methoxyphenyl 2,3-di-O-benzoyl-4-O-(α-D-galactopyranosyl)-β-D-galactopyranoside | 176165-23-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 2,3-di-O-benzoyl-4-O-(α-D-galactopyranosyl)-β-D-galactopyranoside
• CAS: 176165-23-4
• 化学式: C₃₃H₃₆O₁₄
• 分子量: 656.64
• InChiKey: SNRZNKIBPBVNCN-KIHGUMFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  199.9
• 氢给体数：
  5.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 p-methoxyphenyl 2,3-di-O-benzoyl-4-O-(α-D-galactopyranosyl)-β-D-galactopyranoside 以 吡啶 为溶剂， 以89%的产率得到p-methoxyphenyl 6-O-acetyl-2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Double-Chain Bis-Sulfone Neoglycolipids of the 2-, 3-, and 6-Deoxyglobotrioses

  摘要：

  Partially protected 2-(trimethylsilyl)ethyl 2- and 3-deoxyglucosides and 6-deoxylactoside were synthesised via various routes and glycosylated with galabiosyl and galactosyl donors to give the corresponding deoxytrisaccharides. Removal of the protecting groups gave the 2-(trimethylsilyl)ethyl 2-, 3-, and 6-deoxyglobotriosides. Transformation of the protected trisaccharides into trichloroacetimidates, via the corresponding hemiacetals, proceeded in similar to 80% overall yield. Glycosylation of 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propanol with the trisaccharidic trichloroacetimidates, in 72-79% yield, followed by removal of protecting groups, gave the title neoglycolipids.

  DOI：

  10.1021/jo951914k
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 palladium on activated charcoal 2,3,5-三甲基吡啶 、 盐酸 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 50.5h， 生成 p-methoxyphenyl 2,3-di-O-benzoyl-4-O-(α-D-galactopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Double-Chain Bis-Sulfone Neoglycolipids of the 2-, 3-, and 6-Deoxyglobotrioses

  摘要：

  Partially protected 2-(trimethylsilyl)ethyl 2- and 3-deoxyglucosides and 6-deoxylactoside were synthesised via various routes and glycosylated with galabiosyl and galactosyl donors to give the corresponding deoxytrisaccharides. Removal of the protecting groups gave the 2-(trimethylsilyl)ethyl 2-, 3-, and 6-deoxyglobotriosides. Transformation of the protected trisaccharides into trichloroacetimidates, via the corresponding hemiacetals, proceeded in similar to 80% overall yield. Glycosylation of 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propanol with the trisaccharidic trichloroacetimidates, in 72-79% yield, followed by removal of protecting groups, gave the title neoglycolipids.

  DOI：

  10.1021/jo951914k