methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2R,3S,4S,5R,6S)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-[(3R,4S,5R,6S)-4,5-diacetyloxy-6-(2-trimethylsilylethoxy)oxan-3-yl]oxyoxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate | 197144-11-9

• 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 (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2R,3S,4S,5R,6S)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-[(3R,4S,5R,6S)-4,5-diacetyloxy-6-(2-trimethylsilylethoxy)oxan-3-yl]oxyoxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 197144-11-9
• 化学式: C₄₆H₆₉NO₂₇Si
• 分子量: 1096.13
• InChiKey: QCCBOPDKYGOSIK-MRBIJAKRSA-N

物化性质

• 沸点：
  945.7±65.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.0
• 重原子数：
  75
• 可旋转键数：
  33
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  348
• 氢给体数：
  1
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2R,3S,4S,5R,6S)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-[(3R,4S,5R,6S)-4,5-diacetyloxy-6-(2-trimethylsilylethoxy)oxan-3-yl]oxyoxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以100%的产率得到methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2R,3S,4S,5R,6S)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-[(3R,4S,5R)-4,5-diacetyloxy-6-hydroxyoxan-3-yl]oxyoxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  Synthesis of XylβCer, Galβ1−4XylβCer, NeuAcα2−3Galβ1−4XylβCer and the Corresponding Lactone and Lactam Trisaccharides

  摘要：

  2-(Trimethylsilyl)ethyl 2-O-benzoyl- and 2,3-di-O-acetyl-beta-D-xylopyranosides (12 and 14) were synthesized in high yields and subjected to glycosylation with various glycosyl donors. Galactosylation of 12 gave the xylose analogue of TMSEt lactoside (3), which was transformed into the glycosyl acceptor 19. Sialylation then gave the xylose analogue of G(M3) trisaccharide (5). The TMSEt glycosides 10, 25, and 32 were transformed into the corresponding trichloroacetimidates, which were used for glycosylation of an azidosphingosine derivative. The resulting sphingosyl glycosides were transformed into the title ceramides. Treatment of NeuAc alpha 2-3Gal beta 1-4Xyl beta Cer (5) with acetic acid gave the corresponding l''-2'-lactone 7. Glycosylation of 12 or 14 with a G(M4)-lactam donor (40) gave the xylose analogue of G(M3)-lactam (42). There was a 3-fold increase in the formation of GAG chains in the presence of 0.5 mu M Xyl beta Cer (2) in the medium.

  DOI：

  10.1021/jo970298k
• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-α-D-木吡喃糖苷溴 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 甲磺酰溴 、 三氟甲磺酸 、 MS 300AW 、 四丁基氟化铵 、 sodium methylate 、 silver trifluoromethanesulfonate 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 二异丙胺 、 mercury dibromide 、 mercury(II) oxide 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 93.75h， 生成 methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2R,3S,4S,5R,6S)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-[(3R,4S,5R,6S)-4,5-diacetyloxy-6-(2-trimethylsilylethoxy)oxan-3-yl]oxyoxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  Synthesis of XylβCer, Galβ1−4XylβCer, NeuAcα2−3Galβ1−4XylβCer and the Corresponding Lactone and Lactam Trisaccharides

  摘要：

  2-(Trimethylsilyl)ethyl 2-O-benzoyl- and 2,3-di-O-acetyl-beta-D-xylopyranosides (12 and 14) were synthesized in high yields and subjected to glycosylation with various glycosyl donors. Galactosylation of 12 gave the xylose analogue of TMSEt lactoside (3), which was transformed into the glycosyl acceptor 19. Sialylation then gave the xylose analogue of G(M3) trisaccharide (5). The TMSEt glycosides 10, 25, and 32 were transformed into the corresponding trichloroacetimidates, which were used for glycosylation of an azidosphingosine derivative. The resulting sphingosyl glycosides were transformed into the title ceramides. Treatment of NeuAc alpha 2-3Gal beta 1-4Xyl beta Cer (5) with acetic acid gave the corresponding l''-2'-lactone 7. Glycosylation of 12 or 14 with a G(M4)-lactam donor (40) gave the xylose analogue of G(M3)-lactam (42). There was a 3-fold increase in the formation of GAG chains in the presence of 0.5 mu M Xyl beta Cer (2) in the medium.

  DOI：

  10.1021/jo970298k