2,3,4-tri-O-acetyl-β-D-xylopyranosyl-(1→4)-2,3-di-O-acetyl-α-L-rhamnopyranosyl-(1→2)-3,4-di-O-acetyl-α-D-fucopyranosyl trichloroacetimidate | 1481699-55-1

• 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: 2,3,4-tri-O-acetyl-β-D-xylopyranosyl-(1→4)-2,3-di-O-acetyl-α-L-rhamnopyranosyl-(1→2)-3,4-di-O-acetyl-α-D-fucopyranosyl trichloroacetimidate
• 英文别名: Xyl2Ac3Ac4Ac(b1-4)Rha2Ac3Ac(a1-2)D-Fuc3Ac4Ac(a)-O-C(NH)CCl3；[(3R,4S,5R,6S)-4,5-diacetyloxy-6-[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-[(2R,3R,4S,5S,6R)-4,5-diacetyloxy-6-methyl-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxy-2-methyloxan-3-yl]oxyoxan-3-yl] acetate
• CAS: 1481699-55-1
• 化学式: C₃₃H₄₄Cl₃NO₂₀
• 分子量: 881.066
• InChiKey: FZBYQTGRESOKIE-NONZPGANSA-N

物化性质

• 沸点：
  750.4±70.0 °C(predicted)
• 密度：
  1.56±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  57
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  263
• 氢给体数：
  1
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-β-D-xylopyranosyl-(1→4)-2,3-di-O-acetyl-α-L-rhamnopyranosyl-(1→2)-3,4-di-O-acetyl-α-D-fucopyranosyl trichloroacetimidate 、 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以60%的产率得到
  参考文献：
  名称：

  Synthesis of QS-21-Based Immunoadjuvants

  摘要：

  Three structurally defined QS-21-based immune adjuvant candidates (2a-2c) have been synthesized. Application of the two-stage activation glycosylation approach utilizing allyl glycoside building blocks improved the synthetic accessibility of the new adjuvants. The efficient synthesis and establishment of the stand-alone adjuvanticity of the examined synthetic adjuvant (2b) open the door to the pursuit of a new series of structurally defined QS-saponin-based synthetic adjuvants.

  DOI：

  10.1021/jo402118j
• 作为产物：
  描述：

  allyl D-fucopyranoside 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 氢气 、 sodium methylate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 15.49h， 生成 2,3,4-tri-O-acetyl-β-D-xylopyranosyl-(1→4)-2,3-di-O-acetyl-α-L-rhamnopyranosyl-(1→2)-3,4-di-O-acetyl-α-D-fucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of QS-21-Based Immunoadjuvants

  摘要：

  Three structurally defined QS-21-based immune adjuvant candidates (2a-2c) have been synthesized. Application of the two-stage activation glycosylation approach utilizing allyl glycoside building blocks improved the synthetic accessibility of the new adjuvants. The efficient synthesis and establishment of the stand-alone adjuvanticity of the examined synthetic adjuvant (2b) open the door to the pursuit of a new series of structurally defined QS-saponin-based synthetic adjuvants.

  DOI：

  10.1021/jo402118j