allyl 2,3,5-tri-O-acetyl-β-D-apiofuranosyl-(1→3)-2,4-di-O-pivaloyl-β-D-xylopyranosyl-(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-D-fucopyranoside | 1481699-52-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,5-tri-O-acetyl-β-D-apiofuranosyl-(1→3)-2,4-di-O-pivaloyl-β-D-xylopyranosyl-(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-D-fucopyranoside
• 英文别名: [(3R,4S,5R,6S)-6-[[(3aR,4S,6S,7S,7aR)-4-[[(3aS,4R,6S,7R,7aS)-2,2,4-trimethyl-6-prop-2-enoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-4-[(2S,3R,4S)-3,4-diacetyloxy-4-(acetyloxymethyl)oxolan-2-yl]oxy-5-(2,2-dimethylpropanoyloxy)oxan-3-yl] 2,2-dimethylpropanoate
• CAS: 1481699-52-8
• 化学式: C₄₇H₇₂O₂₂
• 分子量: 989.075
• InChiKey: OARSYJVYYHIJMI-ZTCKOODZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  69
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  242
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  allyl 2,3,5-tri-O-acetyl-β-D-apiofuranosyl-(1→3)-2,4-di-O-pivaloyl-β-D-xylopyranosyl-(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-D-fucopyranoside 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 氢气 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.75h， 生成 2,3,5-tri-O-acetyl-β-D-apiofuranosyl-(1→3)-2,4-di-O-acetyl-β-D-xylopyranosyl-(1→4)-2,3-O-diacetyl-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
• 作为产物：
  描述：

  allyl D-fucopyranoside 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 9.16h， 生成 allyl 2,3,5-tri-O-acetyl-β-D-apiofuranosyl-(1→3)-2,4-di-O-pivaloyl-β-D-xylopyranosyl-(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-D-fucopyranoside
  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