2-O-acetyl-3,4-O-dibenzyl-α-L-rhamnopyranoside | 73983-18-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-acetyl-3,4-O-dibenzyl-α-L-rhamnopyranoside
• 英文别名: 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranose；allyl 3,4-di-O-benzyl-α-L-rhamnopyranoside；2-O-acetyl-3,4-di-O-benzyl-L-rhamnopyranose；[(2R,3R,4R,5S,6S)-2-hydroxy-6-methyl-4,5-bis(phenylmethoxy)oxan-3-yl] acetate
• CAS: 73983-18-3
• 化学式: C₂₂H₂₆O₆
• 分子量: 386.445
• InChiKey: BRCHFKBNPWRFCD-AAZWCJRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-O-acetyl-3,4-O-dibenzyl-α-L-rhamnopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.33h， 生成 4-(1,3-Dioxolan-2-yl)-3-oxabutyl 3,4-di-O-benzyl-2-O-[3,4-di-O-benzyl-2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the Trisaccharide α-l-Rha-(1-2)-α-l-Rha-(1-2)-α-L-Rha with a Dioxolane-Type Spacer-Arm¹

  摘要：

  The trisaccharide alpha-L-Rha-(1-2)-alpha-L-Rha-(1-2)-alpha-L-Rha with a dioxolane-type spacer was obtained by using the trichloroacetimidate method in all of the glycosidation steps. After deprotection, the trisaccharide was coupled to BSA or KLH by reductive amination of the spacer aldehyde group.

  DOI：

  10.1080/07328309608005434
• 作为产物：
  描述：

  在 硫酸 、 sodium hydride 、 C.I.酸性橙108 作用下， 以 溶剂黄146 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.33h， 生成 2-O-acetyl-3,4-O-dibenzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the Trisaccharide α-l-Rha-(1-2)-α-l-Rha-(1-2)-α-L-Rha with a Dioxolane-Type Spacer-Arm¹

  摘要：

  The trisaccharide alpha-L-Rha-(1-2)-alpha-L-Rha-(1-2)-alpha-L-Rha with a dioxolane-type spacer was obtained by using the trichloroacetimidate method in all of the glycosidation steps. After deprotection, the trisaccharide was coupled to BSA or KLH by reductive amination of the spacer aldehyde group.

  DOI：

  10.1080/07328309608005434

文献信息

• 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。
• Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2‐Aryl‐1,3‐dithiane 1‐Oxide ^†
  作者：Lei Cai、Jing Zeng、Ting Li、Ying Xiao、Xiang Ma、Xiong Xiao、Qin Zhang、Lingkui Meng、Qian Wan

  DOI：10.1002/cjoc.201900419

  日期：2020.1

  center at the remote site to the anomeric position. The sulfenyl triflate tethered at the terminus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion, thereby facilitating the title glycosylation. Aside from accommodating broad range functional groups and inactive hemiacetal substrates, the present activation protocol also proved expedient for 1,3‐diol protection. Most

  利用三氟甲磺酸酐（Tf 2O）。通过将高亲硫性启动子系统的高效性与脱水糖基化的逐步效率相结合，该试剂通过C1-半乙缩醛供体进行了分子间的氧代硫代缩醛化反应，以安装一个临时的离去基团，从而使远程位置的瞬变亲电子中心变为异头位置。拴在末端的三氟甲磺酸亚砜在分子内同时活化了硫化物，提供了碳碳鎓离子，从而促进了标题糖基化。除了可容纳广泛的官能团和不活跃的半缩醛底物外，目前的激活方案还证明了对1,3-二醇的保护是合宜的。最重要的是，该方法进一步为将硫化学应用于碳水化合物化学提供了新的视角。
• 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。
• GLYCOCONJUGATES AND USE THEREOF AS VACCINE AGAINST SHIGELLA FLEXNERI SEROTYPE 3a AND X
  申请人：INSTITUT PASTEUR

  公开号：US20150050282A1

  公开（公告）日：2015-02-19

  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.

  本发明涉及从糖衍生物中复制Shigella flexneri 3a和X血清型表位的化合物，以及用于制备疫苗组分的使用方法。更具体地说，本发明的主题涉及新型糖连接化合物，包括下文描述的寡糖或多糖，以及合成这些寡糖或多糖和糖连接物的方法，这些寡糖或多糖的衍生物，含有它们的组合物，以及将糖连接物用于疫苗接种目的的用途。最后，本发明涉及使用一种或多种寡糖或多糖或其共轭物来诊断Shigella flexneri感染的方法。
• Carbon-13 n.m.r.-spectral study of l-rhamnose acetates
  作者：Vince Pozsgay、András Neszmélyi

  DOI：10.1016/s0008-6215(00)85326-4

  日期：——