O-[6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-D-glucopyranosyl] trichloroacetimidate | 544686-96-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-[6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-D-glucopyranosyl] trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Glc(b1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Glc-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(2R,3R,4S,5R)-3,4,5-tribenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methoxy]oxan-2-yl]methyl benzoate
• CAS: 544686-96-6
• 化学式: C₆₃H₅₀Cl₃NO₁₈
• 分子量: 1215.44
• InChiKey: VQXGIRIBXXZASZ-CSAJZRSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  85
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  245
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  O-[6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-D-glucopyranosyl] trichloroacetimidate 在 3 A molecular sieve 、 三氟化硼乙醚 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 1,2-O-isopropylidene-3-O-[6-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl]-sn-glycerol
  参考文献：
  名称：

  A Staphylococcus aureus lipoteichoic acid (LTA) derived structural variant with two diacylglycerol residues

  摘要：

  Based on 1,2-O-isopropylidene-sn-glycerol five chiral building blocks containing differently modified glycerol residues were required for the synthesis of the target molecule 2. One of these building blocks is diacylglyceryl beta-gentiobioside carrying a phosphite residue at 6b-O position. Ligation of these five building blocks led to the desired glycerol phosphate backbone to which D-alanyl residues were attached, thus generating after O-deprotection the target molecule 2, a bisamphiphilic structural variant of Staphylococcus aureus LTA. This compound displayed higher potency in terms of cytokine release by human blood leukocytes than the monoamphiphilic variant LTA. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.055
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)-1,2,3,4-tetra-O-benzoyl-D-glucopyranoside 在 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 O-[6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-D-glucopyranosyl] trichloroacetimidate
  参考文献：
  名称：

  A Staphylococcus aureus lipoteichoic acid (LTA) derived structural variant with two diacylglycerol residues

  摘要：

  Based on 1,2-O-isopropylidene-sn-glycerol five chiral building blocks containing differently modified glycerol residues were required for the synthesis of the target molecule 2. One of these building blocks is diacylglyceryl beta-gentiobioside carrying a phosphite residue at 6b-O position. Ligation of these five building blocks led to the desired glycerol phosphate backbone to which D-alanyl residues were attached, thus generating after O-deprotection the target molecule 2, a bisamphiphilic structural variant of Staphylococcus aureus LTA. This compound displayed higher potency in terms of cytokine release by human blood leukocytes than the monoamphiphilic variant LTA. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.055

文献信息

• Immunomodulating beta-1,6-D-glucans
  申请人：Innate Biotherapeutics, LLC

  公开号：US10266609B2

  公开（公告）日：2019-04-23

  This invention relates to modifications of β-1,6-D-glucans, e.g., structures according to Formula (I), and the ability of these compositions to modulate an immune response.

  这项发明涉及对β-1,6-D-葡聚糖的修饰，例如，符合式（I）的结构，以及这些组合物调节免疫反应的能力。
• IMMUNOMODULATING BETA-1,6-D-GLUCANS
  申请人：ImmuneXcite, Inc.

  公开号：US20170081428A1

  公开（公告）日：2017-03-23

  This invention relates to modifications of β-1,6-D-glucans, e.g., structures according to Formula (I), and the ability of these compositions to modulate an immune response.