dodecyl 6-O-acetyl-β-D-galactopyranoside | 222413-68-5

• 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: dodecyl 6-O-acetyl-β-D-galactopyranoside
• CAS: 222413-68-5
• 化学式: C₂₀H₃₈O₇
• 分子量: 390.518
• InChiKey: VZWRAOHDPLYHIF-LCWAXJCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  27.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  105.45
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  dodecyl 6-O-acetyl-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 水 、 sodium methylate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 dodecyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-β-D-galactopyranoside
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Ganglioside Gm4 Analogs as Potential Immunosuppressive Agents

  摘要：

  An efficient, chemoenzymatic synthesis of ganglioside GM4 analogs having a potent immunosuppressive activity is described. One-step and highly regioselective 6-O-acetylation of long-chain alkyl, 2-(trimethysilyl)ethyl and phenyl 1-thio beta-D-galactopyranosides was performed by using vinyl acetate and lipase PS. The resulting 6-O-acetates (70-93%) were sialylated with methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate promoted by N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH). The 2-(trimethylsilyl)ethyl glycoside derivative was converted to the imidate which was then coupled with dodecan-1-ol, hexadecan-1-ol, and 2-(tetradecyl)hexadecan-1-ol, respectively, to give the protected GM4 derivatives (90-96%). O-Deacylation and saponification of the methyl ester gave the target ganglioside GM4 analogs in high yields.

  DOI：

  10.1080/07328309908543992
• 作为产物：
  描述：

  dodecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 Lipase PS 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 dodecyl 6-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Ganglioside Gm4 Analogs as Potential Immunosuppressive Agents

  摘要：

  An efficient, chemoenzymatic synthesis of ganglioside GM4 analogs having a potent immunosuppressive activity is described. One-step and highly regioselective 6-O-acetylation of long-chain alkyl, 2-(trimethysilyl)ethyl and phenyl 1-thio beta-D-galactopyranosides was performed by using vinyl acetate and lipase PS. The resulting 6-O-acetates (70-93%) were sialylated with methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate promoted by N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH). The 2-(trimethylsilyl)ethyl glycoside derivative was converted to the imidate which was then coupled with dodecan-1-ol, hexadecan-1-ol, and 2-(tetradecyl)hexadecan-1-ol, respectively, to give the protected GM4 derivatives (90-96%). O-Deacylation and saponification of the methyl ester gave the target ganglioside GM4 analogs in high yields.

  DOI：

  10.1080/07328309908543992