2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside | 103082-77-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: 2-(trimethylsilyl)ethyl 2,3,6,2',3',4',6'-hepta-O-acetyl-β-D-lactoside；2-trimethylsilylethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)β-D-glucopyranoside；2-trimethylsilylethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-(2-trimethylsilylethoxy)oxan-2-yl]methyl acetate
• CAS: 103082-77-5
• 化学式: C₃₁H₄₈O₁₈Si
• 分子量: 736.797
• InChiKey: ZYKLZZKXEAIYDL-HUXHOXBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  50
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 在 zinc(II) chloride 1,1-二氯甲醚 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到hepta-O-acetyl-α-lactosyl chloride
  参考文献：
  名称：

  一种简便的一步步骤，将2-（三甲基甲硅烷基）乙基糖苷转化为其糖基氯化物

  摘要：

  在二氯甲烷中存在ZnCl 2，SnCl 4或FeCl 3的情况下，用α，α-二氯甲基甲基醚（DCMME）处理各种受保护的2-（三甲基甲硅烷基）乙基（SE）单糖，二糖和三糖苷和半缩醛糖，得到其相应的1,2-顺式糖基氯化物的收率很高。

  DOI：

  10.1016/0040-4039(90)80119-7
• 作为产物：
  描述：

  lactose octaacetate 在 calcium sulfate 、 碘 、 硫代乙酸 、 mercury dibromide 、 mercury(II) oxide 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 生成 2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  乳糖衍生的新型唾液酸化的路易斯X模仿物的合成和生物学评估。

  摘要：

  唾液酸化的路易斯X（sLe（x））模拟化合物2-（三甲基甲硅烷基）乙基3-O-羧甲基-β-D-吡喃半乳糖基-（1-> 4）-α-L-岩藻糖基-（1- > 6）]-β-D-吡喃葡萄糖苷（2a）已由D-乳糖分14步合成。这种合成的特点是使用Koenigs-Knorr序列中活化的糖基化供体乳糖基碘，半乳糖部分C-3位置的区域选择性衍生化以及岩藻糖α（1-> 6）的立体选择性结构）-乳糖键。测试该模拟物在剪切应力条件下抑制人多形核白细胞（hPMNL）与固定化重组人E-选择素粘附的能力。

  DOI：

  10.1021/jo025579t

文献信息

• Mild and efficient method for the cleavage of benzylidene acetals using HClO4–SiO2 and direct conversion of acetals to acetates
  作者：Geetanjali Agnihotri、Anup Kumar Misra

  DOI：10.1016/j.tetlet.2006.03.133

  日期：2006.5

  HClO4–SiO2 has been used successfully for the deprotection of benzylidene acetals and the direct conversion of benzylidene acetals to the corresponding di-O-acetates. The reactions are very fast and yields are excellent.

  HClO 4 -SiO 2已成功用于亚苄基乙缩醛的脱保护和将亚苄基乙缩醛直接转化为相应的二-O-乙酸酯。反应非常快，收率非常好。
• Iodine: A versatile reagent in carbohydrate chemistry III. Efficient activation of glycosyl halides in combination with DDQ
  作者：K.P.Ravindranathan Kartha、Mahmoud Aloui、Robert A Field

  DOI：10.1016/s0040-4039(96)01995-8

  日期：1996.11

  Iodine, either alone or in combination with DDQ, has been found to serve as a very efficient reagent for the conversion of ‘disarmed’ glycosyl halides into simple 1,2-trans-glycosides. This reagent system represents a practical alternative to traditional heavy metal promoters in glycoside synthesis.

  已经发现碘，无论是单独还是与DDQ结合使用，都可以作为一种非常有效的试剂，用于将“解除武装”的糖基卤化物转化为简单的1,2-反式-糖苷。该试剂系统代表了糖苷合成中传统重金属启动子的实用替代品。
• Methods for generating cytotoxic T cells and treatment of diseases
  申请人：Astra Aktiebolag

  公开号：US06033669A1

  公开（公告）日：2000-03-07

  The present invention relates a novel class of biologically active compounds, to processes for their production and to their use in therapy. More particularly the invention provides immunogenic conjugates useful for generating T cell immunity against tumor-associated carbohydrate structures or against carbohydrate structures expressed on infectious agents and/or infected host cells. The said immunogenic conjugate comprises,(i) a peptide component capable of binding a MHC class I molecule; and (ii) a carbohydrate component having the immunogenic specificity of said carbohydrate structure.

  本发明涉及一种新型的生物活性化合物类别，以及它们的制备过程和在治疗中的使用。更具体地，本发明提供了免疫原性结合物，用于产生针对肿瘤相关碳水化合物结构或针对感染体上表达的碳水化合物结构和/或感染宿主细胞的T细胞免疫力。所述的免疫原性结合物包括：（i）能够结合MHC I类分子的肽组分；和（ii）具有所述碳水化合物结构的免疫原特异性的碳水化合物组分。
• Compositions for generating T cell immunity against carbohydrate
  申请人：Astra Aktiebolag

  公开号：US05807559A1

  公开（公告）日：1998-09-15

  The present invention relates to a novel class of immunologically active compounds, to processes for their production and to their use in therapy. In particular, the invention provides immunogenic peptide-carbohydrate conjugates useful for generating T cell immunity against tumor-associated carbohydrate structures, or against carbohydrate structures expressed on infectious agents and/or infected host cells. The immunogenic conjugate comprises a peptide component capable of binding a MHC class I molecule and a carbohydrate component having the same immunogenic characteristics of the carbohydrate structure on the tumor cell, infectious agent or the infected cells.

  本发明涉及一种新型的免疫活性化合物，其制备过程及其在治疗中的应用。具体而言，本发明提供了免疫原性肽-糖结合物，可用于产生T细胞免疫反应，以对抗肿瘤相关的糖结构，或对抗表达在感染体内的感染性代理和/或感染细胞上的糖结构。免疫原性结合物包括一个肽组分，能够结合MHC I类分子，以及一个糖组分，具有与肿瘤细胞、感染代理或感染细胞上的糖结构相同的免疫原性特征。
• Solvent-free bismuth oxycarbonate-mediated mechanochemical glycosylation: A simple greener alternative to access O-/S-glycosides efficiently
  作者：Kashmir Prasad Sethi、K.P. Ravindranathan Kartha

  DOI：10.1016/j.carres.2016.09.004

  日期：2016.11

  Preparation of a variety of per-O-acylated O- and S-glycosides of a set of commonly encountered mono and disaccharides has been achieved effectively by solvent-free grinding of the corresponding acetylated/benzoylated glycosyl bromide and the desired acceptor alcohol/thiol in the presence of bismuth carbonate in a planetary ball mill. The method is simple, requires short reaction time periods and is practical allowing it to be performed at a milligram-to multi-gram scale as required. In the cases where the product is crystalline, it was often obtained in practically pure form by crystallization (and without the need for chromatographic isolation). (C) 2016 Elsevier Ltd. All rights reserved.