methyl (1R)-1-O-acetyl-7-azido-3,4,5,8-tetra-O-benzyl-7,9-dideoxy-1-C-heptyl-2-thio-D-erythro-α-D-galacto-non-2-ulopyranoside | 1146962-91-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (1R)-1-O-acetyl-7-azido-3,4,5,8-tetra-O-benzyl-7,9-dideoxy-1-C-heptyl-2-thio-D-erythro-α-D-galacto-non-2-ulopyranoside
• CAS: 1146962-91-5
• 化学式: C₄₇H₅₉N₃O₇S
• 分子量: 810.067
• InChiKey: RYARJEKJKVDPPW-YFNMCAGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.78
• 重原子数：
  58.0
• 可旋转键数：
  24.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  121.21
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl (1R)-1-O-acetyl-7-azido-3,4,5,8-tetra-O-benzyl-7,9-dideoxy-1-C-heptyl-2-thio-D-erythro-α-D-galacto-non-2-ulopyranoside 在 sodium hydroxide 、 三甲基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 生成 methyl (1R)-1-O-acetyl-3,4,5,8-tetra-O-benzyl-7,9-dideoxy-1-C-heptyl-7-[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido]-2-thio-D-erythro-α-D-galacto-non-2-ulopyranoside
  参考文献：
  名称：

  林可霉素的S和C（1）取代类似物的合成和评价

  摘要：

  Abstractmagnified imageNew thioglycosides and C(1)‐alkylated thioglycosides (S‐ulosides) of lincomycin were synthesized, and their antibiotic activities were determined. The S‐aryl and S‐arylalkyl analogues 11a–11i were obtained by S‐glycosylation of the sulfoxides 7 with arenethiols, or by S‐alkylation of the thiol 14 with alkyl bromides. Lincomycin derivatives 27, 32a, 32b, 38a, 38b, 44, and 47 were prepared via Henry reaction or Michael addition of the lincosamine‐derived 1‐deoxy‐1‐nitropyranoses 22. The S‐alkyl derivatives showed a similar activity and specificity as lincomycin. Lipophilic S‐uloside analogues were two‐ to fourfold less active than the parent antibiotic, whilst the hydrophilic analogues were inactive.

  DOI：

  10.1002/hlca.200800343
• 作为产物：
  描述：

  甲硫醇 、 (1R)-1,2-di-O-acetyl-7-azido-3,4,5,8-tetra-O-benzyl-7,9-dideoxy-1-C-heptyl-D-erythro-α-D-galacto-non-2-ulopyranose 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以46%的产率得到methyl (1R)-1-O-acetyl-7-azido-3,4,5,8-tetra-O-benzyl-7,9-dideoxy-1-C-heptyl-2-thio-D-erythro-α-D-galacto-non-2-ulopyranoside
  参考文献：
  名称：

  林可霉素的S和C（1）取代类似物的合成和评价

  摘要：

  Abstractmagnified imageNew thioglycosides and C(1)‐alkylated thioglycosides (S‐ulosides) of lincomycin were synthesized, and their antibiotic activities were determined. The S‐aryl and S‐arylalkyl analogues 11a–11i were obtained by S‐glycosylation of the sulfoxides 7 with arenethiols, or by S‐alkylation of the thiol 14 with alkyl bromides. Lincomycin derivatives 27, 32a, 32b, 38a, 38b, 44, and 47 were prepared via Henry reaction or Michael addition of the lincosamine‐derived 1‐deoxy‐1‐nitropyranoses 22. The S‐alkyl derivatives showed a similar activity and specificity as lincomycin. Lipophilic S‐uloside analogues were two‐ to fourfold less active than the parent antibiotic, whilst the hydrophilic analogues were inactive.

  DOI：

  10.1002/hlca.200800343