phenyl 6-O-acetyl-2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-1-thio-β-D-galactopyranoside | 176165-27-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 6-O-acetyl-2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-1-thio-β-D-galactopyranoside
• 英文别名: Gal2Ac3Ac4Ac6Ac(a1-4)[Bz(-2)][Bz(-3)]Gal6Ac(b)-SPh；[(2R,3S,4S,5R,6S)-2-(acetyloxymethyl)-5-benzoyloxy-6-phenylsulfanyl-3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-4-yl] benzoate
• CAS: 176165-27-8
• 化学式: C₄₂H₄₄O₁₇S
• 分子量: 852.867
• InChiKey: NEPNWAHKFIVXHZ-HRXIINBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  60
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  237
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  phenyl 6-O-acetyl-2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.67h， 生成 2-O-benzoyl-3-deoxy-6-O-(p-methoxybenzoyl)-4-O-<6-O-acetyl-2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-D-ribo-hexopyranose
  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：

  苯硫酚 、 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 在 三氟化硼乙醚 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 10.0h， 生成 phenyl 6-O-acetyl-2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-1-thio-β-D-galactopyranoside 、 phenyl 6-O-acetyl-2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-1-thio-α-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