4-methoxyphenyl 6-azido-2,3,4,7-tetrakis-O-[(tert-butyl)dimethylsilyl]-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside | 1146962-42-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxyphenyl 6-azido-2,3,4,7-tetrakis-O-[(tert-butyl)dimethylsilyl]-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside
• CAS: 1146962-42-6
• 化学式: C₃₉H₇₇N₃O₆SSi₄
• 分子量: 828.465
• InChiKey: UAGBTTHTAKAUKY-MXNJPTFHSA-N

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 6-azido-2,3,4,7-tetrakis-O-[(tert-butyl)dimethylsilyl]-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside 在 sodium hydroxide 、 三甲基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 生成
  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：

  4-甲氧基苯硫酚 、 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 以 乙醚 为溶剂， 反应 2.5h， 以60%的产率得到4-methoxyphenyl 6-azido-2,3,4,7-tetrakis-O-[(tert-butyl)dimethylsilyl]-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside
  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