2,4,6-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-D-glucopyranosyl trichloroacetimidate | 209465-77-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,6-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-D-glucopyranosyl trichloroacetimidate
• 英文别名: 6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucosyl)-2,3,4-tri-O-acetylglycosyl trichloroacetimidate；1-O-(2,2,2-trichloroethanimidoyl)-6-O-[O-β-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosyl-(1,6)]-D-glucopyranose 2,3,4-tri-O-acetate；Glc2Ac3Ac4Ac6Ac(b1-6)Glc2Ac3Ac4Ac-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 209465-77-0
• 化学式: C₂₈H₃₆Cl₃NO₁₈
• 分子量: 780.949
• InChiKey: BQWSDTBLBHIXEF-DHDYIENTSA-N

物化性质

• 沸点：
  681.8±65.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  50
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  2,4,6-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  Influence of Subphase Conditions on Interfacial Viscoelastic Properties of Synthetic Lipids with Gentiobiose Head Groups

  摘要：

  The thermodynamic parameters and rheological properties of a synthetic glycolipid with a gentiobiose (O(beta-D-glucopyranosyl)-(1-->6-beta-D-glucopyranoside)) headgroup have been studied at the air/water interface. The phase transition entropy and latent heat were estimated by film balance experiments at various temperatures, whereas dynamic surface moduli (loss and storage modulus) were measured by an interfacial stress rheometer under well-defined thermodynamic conditions. The impact of glucosidic bonding was systematically studied by comparing the measured results to those from the lipid with a lactose (O-(beta-D-galactopyranosyl)-(1-->4-beta-D-glucopyranoside)) headgroup, which possesses the similar monosaccharide composition. We found that the "bent" 1-->6 junction of gentiobiose reduces the lateral intermolecular cooperativity and fluidizes the films in comparison to the lactose lipid monolayer.

  DOI：

  10.1021/jp0367934
• 作为产物：
  描述：

  6-O-trityl-D-glucopyranose 在 吡啶 、 氢溴酸 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 苄胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 73.52h， 生成 2,4,6-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of leptosin, a glycoside isolated from mānuka honey

  摘要：

  The first synthesis of leptosin, a novel glycoside isolated from manuka honey is described. Utilising an acetyl protecting group strategy the glycoside was obtained with excellent anomeric selectivity by deploying a Schmidt glycosylation as a key step. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.042

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。
• 1,3-Dideoxynojirimycin-3-yl glycosides of β-(1→3)- and β-(1→6)-linked gluco-oligosaccharides
  作者：Regine Blattner、Richard H. Furneaux、Zbigniew Pakulski

  DOI：10.1016/j.carres.2006.05.004

  日期：2006.9

  glycosyl trichloroacetimidates as glycosylating agents were used to prepare the five 1,3-dideoxynojirimycin-3-yl β-(1→3)-linked oligo-glucosides ( 1 – 5) and also the β-(1→6)-bonded glucobiose (gentiobiose)-based analogue 6 as potential fungicides. In the course of the work, the β-(1→6), β-(1→6)-linked analogue 8 of 6 and 6- O - and 4- O -β-glucopyranosyl-deoxynojirimycins 7 and 9 , respectively, were also

  摘要使用涉及以O-乙酰化的糖基三氯乙酰亚氨酸酯为糖基化剂的标准化学方法，制备了5种与1,3-二脱氧野oji菌素-3-基β-（1→3）连接的低聚葡糖苷（1-5），以及β-（1→6）键合的葡萄糖二糖（龙胆二糖）基类似物6作为潜在的杀菌剂。在工作过程中，分别由β-（1→6），β-（1→6）连接的6和6-O-和4-O-β-吡喃葡萄糖基-脱氧野oji霉素7和9的类似物8，也产生了。
• 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.