methyl 2,3,9,11-tetradeoxy-9-[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido]-4-thio-D-erythro-α-D-galacto-undec-4-ulopyranosidonitrile | 1146962-69-7

• 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 2,3,9,11-tetradeoxy-9-[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido]-4-thio-D-erythro-α-D-galacto-undec-4-ulopyranosidonitrile
• 英文别名: (2S,4R)-N-[(1R,2R)-1-[(2R,3R,4S,5R,6R)-6-(2-cyanoethyl)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]-2-hydroxypropyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
• CAS: 1146962-69-7
• 化学式: C₂₁H₃₇N₃O₆S
• 分子量: 459.607
• InChiKey: KMILKMPUCKWJFJ-OVBLCIHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  methyl 5,6,7,10-tetra-O-benzyl-2,3,9,11-tetradeoxy-9-[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido]-4-thio-D-erythro-α-D-galacto-undec-4-ulopyranosidonitrile 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以60%的产率得到methyl 2,3,9,11-tetradeoxy-9-[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido]-4-thio-D-erythro-α-D-galacto-undec-4-ulopyranosidonitrile
  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

文献信息

• Synthesis and Evaluation of<i>S</i>- and<i>C(1)</i>-Substituted Analogues of Lincomycin
  作者：Marie-Pierre Collin、Sven N. Hobbie、Erik C. Böttger、Andrea Vasella

  DOI：10.1002/hlca.200800343

  日期：2009.2

  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.