2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-1,2,4-tri-O-acetyl-D-glucopyranoside | 490025-83-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-1,2,4-tri-O-acetyl-D-glucopyranoside
• 英文别名: 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-1,2,4-tri-O-acetyl-α,β-D-glucopyranose；2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1→6)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1→3)]-1,2,4-tri-O-acetyl-D-glucopyranose；Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a1-3)[Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a1-6)]Glc1Ac2Ac4Ac；[(2R,3R,4S,5S,6S)-3,4,5-tribenzoyloxy-6-[[(2R,3R,4S,5R)-3,5,6-triacetyloxy-4-[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxan-2-yl]methyl benzoate
• CAS: 490025-83-7
• 化学式: C₈₀H₇₀O₂₇
• 分子量: 1463.42
• InChiKey: LTTSKAPSZOPDGJ-YXYJJXLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  107
• 可旋转键数：
  37
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  335
• 氢给体数：
  0
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-1,2,4-tri-O-acetyl-D-glucopyranoside 在 氢溴酸 、 乙酸酐 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  单去糖皂苷与亚麻酸，麦角苦参素和皂苷元糖苷配基以及某些C-28酯衍生物的合成，配制和佐剂作用。

  摘要：

  为了发现一种新的合成疫苗佐剂，进行了二十三碳精，gypsogenin和齐墩果酸受体与二糖和三糖供体的糖基化反应，以生成一系列天然产物QS-21的模拟物。将皂苷与磷脂酰胆碱和胆固醇一起配制，并通过透射电子显微镜分析其结构。3‐ O‐（Man p（1 → 3）Glc p角姜黄素配制成时会产生大量环状胶束，而C-28胆碱酯衍生物更倾向于自组装且不与脂质体相互作用。当单独存在胆固醇和磷脂时，胆碱酯衍生物会产生纳米晶棒或螺旋胶束。然后使用激活标记MHC II类和CD86在小鼠骨髓树突状细胞中评估了修饰糖的立体化学和糖苷配基对皂苷的免疫刺激作用的作用。活性最高的皂苷3‐ O‐（Man p（1 → 3）Glc p）七面发生素在细胞培养物中高浓度时具有刺激性，但在体内并没有转化为强烈的反应。

  DOI：

  10.1002/open.201500149
• 作为产物：
  描述：

  乙酸酐 、 在 吡啶 作用下， 反应 2.0h， 以1023 mg的产率得到2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-1,2,4-tri-O-acetyl-D-glucopyranoside
  参考文献：
  名称：

  A facile synthesis of the tetrasaccharide repeating unit of mannoglucan from Microellobosporia grisea

  摘要：

  A facile synthesis of the tetrasaccharide repeating unit of mannoglucan from Microellobosporia grisea was achieved through coupling of 4,6-O-benzylidene-1,2-O-ethylidene-alpha-D-glucopyranose with per-O-benzoylated mannopyranosyl trichloroacetimidate, followed by debenzylidenation, selective 6-O-mannopyranosylation, then hydrolysis of the 1,2-O-ethylidene group, 1,2-O-acetylation and conversion to the 1-trichloroacetimidate, and subsequent condensation of the activated trisaccharide with allyl 2,3,6-tri-0-benzoyl-alpha-D-glucopyranoside. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00160-9

文献信息

• Synthesis of mannose-containing analogues of (1→6)-branched (1→3)-glucohexaose (I)
  作者：Zicheng Wu、Fanzuo Kong

  DOI：10.1016/s0008-6215(03)00263-5

  日期：2003.8

  alpha-D-Manp-(1-->3)-[alpha-D-Manp-(1-->6)]-alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[alpha-D-Manp-(1-->6)]-D-Glcp and alpha-D-Manp-(1-->3)-[beta-D-Glcp-(1-->6)]-alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)[-alpha-D-Manp-(1-->6)]-D-Glcp were synthesized in a regio- and stereoselective way as the mannose-containing analogues of the immunomodulating beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1 -->3)-[beta-D-Glcp-(1-->6)]-D-Glcp. (C) 2003 Elsevier Ltd. All rights reserved.