3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α/β-D-glucopyranose trichloroacetimidate | 161545-19-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α/β-D-glucopyranose trichloroacetimidate
• 英文别名: trichloroacetimidoyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranoside；3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl trichloroacetimidate；3,4,6-tri-O-acetyl-2-deoxy-2-N-trichloroacetyl-α-D-glucopyranosyl trichloroacetimidate；3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-alpha-D-glucopyranose trichloroacetimidate；[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-[(2,2,2-trichloroacetyl)amino]-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 161545-19-3
• 化学式: C₁₆H₁₈Cl₆N₂O₉
• 分子量: 595.045
• InChiKey: IRYYFLMRFPICED-LZQZFOIKSA-N

物化性质

• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  150
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α/β-D-glucopyranose trichloroacetimidate 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-L-rhamnopyranosyl trichloroacetamidate
  参考文献：
  名称：

  嵌段途径的O-特异性多糖的片段志贺氏菌˚F lexneri血清型2A：支链重复单元的二聚体的一个十糖代表汇集合成1

  摘要：

  的d “甲”乙“ （E ” ）C ' DAB（E）C十糖代表的二聚物的帧偏移的五糖重复的O-特异性多糖的单元弗氏志贺菌2a中被冷凝合成作为它的甲基糖苷五糖给体（d '甲'乙' （E ' ）C “）和五糖受体（DAB（E）C -OMe）。通往这两个构建块的多条融合路线，涉及AB链接或BC链接作为断开位置，与线性策略相比进行了评估。后者是优选的。它基于三氯乙酰亚胺酸化学的使用。设计目标支链低聚糖，以探测保护性单克隆抗体在天然多糖分子水平上的识别。

  DOI：

  10.1021/jo035125b
• 作为产物：
  描述：

  2-amino-2-deoxy-1,3,4,6-tetra-O-(trimethylsilyl)-α-D-glucopyranose 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α/β-D-glucopyranose trichloroacetimidate
  参考文献：
  名称：

  -O-三甲基甲硅烷基化糖的非端基的选择性乙酰化

  摘要：

  糖的羟基的选择性修饰由于其近乎相对的反应性而一直是一个长期的挑战。本文中，我们报道了TMSOTf催化的几种过O -TMS保护的糖底物的非异头羟基的选择性乙酰化，同时不影响其异头基团。除了本身具有通用性之外，可以将完整的异头O -TMS基团官能化，以提供关键的糖前体，如亚氨酸酯供体，否则可以通过逐步的异头脱保护-官能化程序进行合成。

  DOI：

  10.1021/acs.joc.0c02813
• 作为试剂：
  描述：

  三氟甲磺酸三甲基硅酯 、 (2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid amide 在 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α/β-D-glucopyranose trichloroacetimidate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以15%的产率得到allyl 3,4-di-O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-2-O-tert-butyldimethylsilyl-β-D-glucopyranosiduronamide
  参考文献：
  名称：

  A Moenomycin-type Structural Analogue of Lipid II some possible mechanisms of the mode of action of transglycosylase inhibitors can be discarded

  摘要：

  The transglycosylation step in the peptidoglycan biosynthesis belongs to the general class of glycosyltransferase-catalyzed reactions. The structural analogue 2 of moenomycin A has been synthesized and has been found to be antibiotically inactive. The assumption that moenomycin-type transglycosylase inhibitors such as 1 bind at the donor site of the enzyme and that their mode of action is the result of the high stability of the sugar --> phosphate bond seems to be ruled out by the present results.

  DOI：

  10.1002/prac.19973390162

文献信息

• The use of 2-deoxy-2-trichloroacetamido-d-glucopyranose derivatives in syntheses of oligosaccharides
  作者：Géraldine Blatter、Jean-Marie Beau、Jean-Claude Jacquinet

  DOI：10.1016/0008-6215(94)84038-5

  日期：1994.7

  trichloroacetimidate and its O-benzylated analogue were tested as glycosyl donors in the reaction with a set of sugar acceptors unsubstituted on O-3 and O-4, typically encountered in the synthesis of oligosaccharides. Glycosides were obtained in good to excellent yields with only a slight excess (1.1-1.2 equiv) of the donor, and with a high degree of 1,2-trans stereoselectivity. The corresponding 2-(trich

  测试了3,4,6-三-O-乙酰基-2-脱氧-2-三氯乙酰氨基-α-D-吡喃葡糖基三氯乙酰亚氨酸酯及其O-苄基类似物与一组未在O上取代的糖受体在反应中的糖基供体-3和O-4，通常在寡糖合成中遇到。以良好至极好的收率获得糖苷，仅略微过量（1.1-1.2当量）的供体，并具有高度的1，2-反式立体选择性。假定相应的2-（三氯甲基）恶唑啉鎓离子是主要的反应性中间体。在中性条件下，通过用三丁基锡烷还原，二糖产物中的N-三氯乙酰基很容易转化为N-乙酰基。
• Glycoconjugates and use thereof as vaccine against Shigella flexneri serotype 3a and X
  申请人：Mulard Laurence

  公开号：US08815239B2

  公开（公告）日：2014-08-26

  The present invention relates to compounds derived from sugars which reproduce the epitopes of Shigella flexneri serotypes 3a and X and to the use thereof for the preparation of vaccine compositions. More specifically, the subject matter of the present invention relates to novel glycoconjugated compounds comprising oligosaccharides or polysaccharides described hereinafter, to the method for synthesizing these oligosaccharides or polysaccharides and glycoconjugates, to derivatives of these oligosaccharides or polysaccharides, to compositions containing same, and also to the use of the glycoconjugates for vaccination purposes. Finally, the present invention relates to methods for diagnosing a Shigella flexneri infection using one or more oligosaccharides or polysaccharides or conjugates thereof.

  本发明涉及从糖类衍生的化合物，其重现志贺氏菌弗氏菌血清型3a和X的表位，并且涉及将其用于制备疫苗组合物。更具体地，本发明涉及包括下文描述的寡糖或多糖的新型糖结合化合物，用于合成这些寡糖或多糖和糖结合物的方法，这些寡糖或多糖的衍生物，含有这些衍生物的组合物，以及将糖结合物用于疫苗目的的用途。最后，本发明涉及使用一个或多个寡糖或多糖或其结合物诊断志贺氏菌弗氏菌感染的方法。
• Synthesis of LeaLex oligosaccharide fragments and efficient one-step deprotection
  作者：An Wang、France-Isabelle Auzanneau

  DOI：10.1016/j.carres.2010.03.038

  日期：2010.6

  bromide. Thus, syntheses of the protected tri- and tetrasaccharides were achieved easily and efficiently using known building blocks. Of particular interest, we also report that these protected oligosaccharides were submitted to dissolving metal conditions (Na-NH(3)) to provide in one single step the corresponding deprotected compounds. Under these conditions all protecting groups (O-acyl, benzylidene

  我们在这里描述了肿瘤相关的碳水化合物抗原Le（a）Le（x）的两个寡糖片段的合成。线性乳糖N-三糖I：β-D-Galp-（1-> 4）-β-D-GlcNAcp-（1-> 3）-β-D-Galp-OMe是已知的化合物，这是第一个报道的支链四糖β-D-GlcNAcp-（1-> 3）-β-D-Galp-（1-> 4）-[α-1-Fucp-（1-> 3）]-β-D-GlcNAcp-OMe。我们的合成方案涉及使用在0摄氏度下用过量TMSOTf活化的N-三氯乙酰化三氯乙酰亚氨酸酯氨基葡萄糖供体在O-3上半乳糖基残基的O-3糖基化和用过量BF（3）.OEt（2）活化以糖基化的三氯乙酰亚氨基半乳糖基供体的糖基化O-3或O-4的氨基葡萄糖残基。葡糖胺受体在O-3处的岩藻糖基化反应是通过用溴化铜（II）和溴化四丁基铵活化的硫代葡糖苷供体完成的。因此，使用已知的结构单元容易且有效地实现了被保护的三糖和四糖的合成
• Synthesis of Two Tetra- and Four Pentasaccharide Fragments of<i>Shigella flexneri</i>Serotypes 3a and X O-Antigens from a Common Tetrasaccharide Intermediate
  作者：Julien Boutet、Laurence A. Mulard

  DOI：10.1002/ejoc.200800693

  日期：2008.11

  Ac→2]-α-L-Rhap-(1→3)-β-D-GlcpNAc-(1→}n ((E)ABAcCD)n polymer were synthesized as their propyl glycosides by use of a common fully protected (E)ABAcC intermediate (9). Tetrasaccharide 9 derived from the condensation of an EA donor and a BAcC acceptor. Partial and full deprotection gave free tetrasaccharides (E)ABAcC and (E)ABC, respectively. Alternatively, 9 was converted into a trichloroacetimidate

  所得受体与 D 供体的糖基化，以及随后的部分或全部脱保护，得到支链五糖 D(E)ABAcC 和 D(E)ABC。所有目标都是志贺氏菌 3a 的 O 抗原的一部分，这是一种流行的血清型。非 O-乙酰化寡糖由 S.flexneri 血清型 X O-抗原共有。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• GLYCOCONJUGATES AND USE THEREOF AS VACCINE AGAINST SHIGELLA FLEXNERI SEROTYPE 3A AND X
  申请人：Mulard Laurence

  公开号：US20100239584A1

  公开（公告）日：2010-09-23

  The present invention relates to compounds derived from sugars which reproduce the epitopes of Shigella flexneri serotypes 3a and X and to the use thereof for the preparation of vaccine compositions. More specifically, the subject matter of the present invention relates to novel glycoconjugated compounds comprising oligosaccharides or polysaccharides described hereinafter, to the method for synthesizing these oligosaccharides or polysaccharides and glycoconjugates, to derivatives of these oligosaccharides or polysaccharides, to compositions containing same, and also to the use of the glycoconjugates for vaccination purposes. Finally, the present invention relates to methods for diagnosing a Shigella flexneri infection using one or more oligosaccharides or polysaccharides or conjugates thereof.

  本发明涉及从糖类衍生的化合物，这些化合物重现Shigella flexneri血清型3a和X的表位，并且用于制备疫苗组合物。更具体地，本发明涉及包含下文描述的寡糖或多糖的新型糖结合化合物，用于合成这些寡糖或多糖和糖结合物的方法，这些寡糖或多糖的衍生物，含有这些化合物的组合物，以及将糖结合物用于疫苗目的的用途。最后，本发明涉及使用一个或多个寡糖或多糖或其共轭物诊断Shigella flexneri感染的方法。