3-O-allyl-2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-1,2-O-isopropylidene-α-D-glucofuranose | 612060-33-0

• 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: 3-O-allyl-2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-1,2-O-isopropylidene-α-D-glucofuranose
• CAS: 612060-33-0
• 化学式: C₅₈H₆₂O₂₃
• 分子量: 1127.12
• InChiKey: WYPIGXANBPGLLE-FPLUWZOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  81.0
• 可旋转键数：
  22.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  278.17
• 氢给体数：
  1.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  3-O-allyl-2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-1,2-O-isopropylidene-α-D-glucofuranose 在 吡啶 、 palladium dichloride 作用下， 以 甲醇 为溶剂， 反应 27.0h， 生成 2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-5-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis of Analogues of (1 → 6)‐Branched (1 → 3)‐Glucohexaose

  摘要：

  beta-D-Galp-(1-->3)-[beta-D-Galp-(1-->6)-]alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[alpha-D-Manp-(1-->6)-]D-Glcp 16 and beta-D-Galp-(1-->3)-[beta-D-Glcp-(1-->6)-]alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[alpha-D-Manp-(1-->6)-]D-Glcp 18 were synthesized as the analogues of the immunomodulator 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 through coupling of trisaccharide donors 8 and 13 with trisaccharide acceptor 14 followed by deprotection, respectively.

  DOI：

  10.1081/car-200045260
• 作为产物：
  描述：

  [(2R,3R,4S,5S,6S)-3,4,5-三苯甲酰氧基-6-(2,2,2-三氯亚氨代乙酰)氧基-四氢吡喃-2-基]甲基苯甲酸酯 、 3-O-allyl-2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-1,2-O-isopropylidene-α-D-glucofuranose 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以64%的产率得到3-O-allyl-2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis of Analogues of (1 → 6)‐Branched (1 → 3)‐Glucohexaose

  摘要：

  beta-D-Galp-(1-->3)-[beta-D-Galp-(1-->6)-]alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[alpha-D-Manp-(1-->6)-]D-Glcp 16 and beta-D-Galp-(1-->3)-[beta-D-Glcp-(1-->6)-]alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[alpha-D-Manp-(1-->6)-]D-Glcp 18 were synthesized as the analogues of the immunomodulator 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 through coupling of trisaccharide donors 8 and 13 with trisaccharide acceptor 14 followed by deprotection, respectively.

  DOI：

  10.1081/car-200045260

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.