6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-D-glucopyranose
• 英文别名: 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-D-glucopyranoside；Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Glc(b1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Glc；[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(2R,3R,4S,5R)-3,4,5-tribenzoyloxy-6-hydroxyoxan-2-yl]methoxy]oxan-2-yl]methyl benzoate
• 化学式: C₆₁H₅₀O₁₈
• 分子量: 1071.06
• InChiKey: JONYQDFKSAJUIU-YYAPYIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  79
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  232
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-D-glucopyranose 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到2,3,4,2',3',4',6'-hepta-O-benzoyl-α-gentiobiosyl bromide
  参考文献：
  名称：

  从 Oroxylum indium 的种子中分离出的天然黄酮苷、oroxins C 和 D 的简明合成和抗糖尿病活性

  摘要：

  从 Oroxylum indicum 的种子中分离出的天然黄酮苷类化合物 C (1) 和 D (2) 的首次简洁合成是通过收敛策略有效实现的。这 ...

  DOI：

  10.1177/1747519820927966
• 作为产物：
  描述：

  1,2,3,4-tetra-O-benzoyl-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氨 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-D-glucopyranose
  参考文献：
  名称：

  Total Synthesis of the Antiallergic Naphtho-α-pyrone Tetraglucoside, Cassiaside C₂, Isolated from Cassia Seeds

  摘要：

  Toralactone 9-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1, cassiaside C-2) isolated from Cassia obtusifolia L. and showing strong antiallergic activity, was concisely synthesized employing glycosyl trifluoroacetimidates as glycosylation agents. The unique naphtho-alpha-pyrone structure of toralactone (5) was constructed by condensation of orsellinate 8 with pyrone 9 in the presence of LDA as developed by Staunton and co-workers. The naphthol of toralactone showed minimal reactivity as an acceptor and was screened with various glycosyl donors. It is finally concluded that sacrifice of an excess amount of the trifluoroacetimidate or trichloroacetimidate donors (6f/6g, 6.0 equiv) in the presence of a catalytic amount of TMSOTf (0.05 and 0.3 equiv, respectively) afforded excellent yields of the coupling product, which was otherwise only a minor product under a variety of conditions examined.

  DOI：

  10.1021/jo034223u

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。
• [EN] ß-1,6-GLUCAN TRASTUZUMAB ANTIBODY CONJUGATES<br/>[FR] CONJUGUÉS D'ANTICORPS DE TRASTUZUMAB SS-1,6-GLUCANE
  申请人：INNATE BIOTHERAPEUTICS LLC

  公开号：WO2018106644A1

  公开（公告）日：2018-06-14

  The present invention encompasses embodiments in which trastuzumab or a related trastuzumab antibody is conjugated to β-1,6-glucan oligomers. Thus, the present invention includes, among other things, compositions including trastuzumab conjugated to one or more β-1,6-glucan oligomers. The present invention further includes, among other things, methods of making and/or using such β-1,6-glucan conjugates. In certain embodiments, a β-1,6-glucan conjugate of the present invention is useful as a therapeutic or in a method of therapy.

  本发明涵盖了将曲妥珠单抗或相关的曲妥珠抗体与β-1,6-葡聚糖寡聚体结合的实施方式。因此，本发明包括了包含曲妥珠与一个或多个β-1,6-葡聚糖寡聚体结合的组合物等内容。本发明还包括了制备和/或使用这种β-1,6-葡聚糖共轭物的方法等内容。在某些实施方式中，本发明的β-1,6-葡聚糖共轭物可用作治疗或治疗方法。
• [EN] β-1,6-GLUCAN CETUXIMAB ANTIBODY CONJUGATES<br/>[FR] CONJUGUÉS DE Β-1,6-GLUCANE ET DE L'ANTICORPS CÉTUXIMAB
  申请人：IMMUNEXCITE INC

  公开号：WO2016196682A1

  公开（公告）日：2016-12-08

  The present invention encompasses embodiments in which cetuximab or a related cetuximab antibody is conjugated to β-1,6-glucan oligomers. Thus, the present invention includes, among other things, compositions including cetuximab conjugated to one or more β-1,6-glucan oligomers. The present invention further includes, among other things, methods of making and/or using such β-1,6-glucan conjugates. In certain embodiments, a β-1,6-glucan conjugate of the present invention is useful as a therapeutic or in a method of therapy.

  本发明涵盖了将Cetuximab或相关的Cetuximab抗体与β-1,6-葡聚糖寡聚体结合的实施例。因此，本发明包括将Cetuximab与一个或多个β-1,6-葡聚糖寡聚体结合的组合物，以及制备和/或使用这样的β-1,6-葡聚糖结合物的方法等。在某些实施例中，本发明的β-1,6-葡聚糖结合物可用作治疗或治疗方法中的治疗剂。
• Stereoselective Synthesis of β-glycosyl Esters via 1-Hydroxybenzotriazole Mediated Acylation of Glycosyl Hemiacetals
  作者：Zijing Liu、Dan Liu、Dapeng Zhu、Biao Yu

  DOI：10.1021/acs.orglett.3c01750

  日期：2023.7.21

  Highly stereoselective access to β-glycosyl esters was disclosed, employing 1-hydroxybenzotriazole (HOBt) mediated esterification of glycosyl hemiacetals in the presence of EDCI and 1,4-diazabicyclo[2.2.2]octane (DABCO). Mechanistic studies indicated a dynamic kinetic acylation pathway. In addition, a stereoretentive esterification of glycosyl hemiacetals with tert-butyloxycarbonyl ortho-hexynylbenzoate

  公开了在 EDCI 和 1,4-二氮杂双环[2.2.2]辛烷 (DABCO) 存在下，采用 1-羟基苯并三唑 (HOBt) 介导的糖基半缩醛酯化，高度立体选择性地获得 β-糖基酯。机理研究表明动态酰化途径。此外，还报道了糖基半缩醛与叔丁氧羰基邻己炔基苯甲酸酯和DMAP的立体保持酯化。
• A Staphylococcus aureus lipoteichoic acid (LTA) derived structural variant with two diacylglycerol residues
  作者：A STADELMAIER、I FIGUEROAPEREZ、S DEININGER、S VONAULOCK、T HARTUNG、R SCHMIDT

  DOI：10.1016/j.bmc.2006.05.055

  日期：2006.9.15

  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.