(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)ethene | 799267-94-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)ethene
• 英文别名: 2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-galactopyranosylethene；(2R,3S,4R,5S,6R)-2-ethenyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 799267-94-0
• 化学式: C₃₆H₃₈O₅
• 分子量: 550.695
• InChiKey: NZOJIBOFXCAAOQ-DQROVBKRSA-N

物化性质

• 沸点：
  650.0±55.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)ethene 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 4-二甲氨基吡啶 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 120.67h， 生成 4-C-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1-O-palmitoyl-2(S)-O-stearoyl-3-E-butene
  参考文献：
  名称：

  Efficient Synthesis of a C-Analogue of the Immunogenic Bacterial Glycolipid BbGL2

  摘要：

  Synthesis of a C-analogue of bacterial glycolipid BbGL2 is reported using Grignard reaction of in situ generated beta-galactosyl iodide and subsequent olefin cross metathesis reaction of C-vinyl galactoside as key steps.

  DOI：

  10.1021/ol062354m
• 作为产物：
  描述：

  Α-D-乳酸吡喃糖苷甲酯 在 碘代三甲硅烷 、 硫酸 、 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 11.08h， 生成 (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)ethene
  参考文献：
  名称：

  Efficient Synthesis of a C-Analogue of the Immunogenic Bacterial Glycolipid BbGL2

  摘要：

  Synthesis of a C-analogue of bacterial glycolipid BbGL2 is reported using Grignard reaction of in situ generated beta-galactosyl iodide and subsequent olefin cross metathesis reaction of C-vinyl galactoside as key steps.

  DOI：

  10.1021/ol062354m

文献信息

• Novel synthetic C-glycolipids, their synthesis and use to treat infections, cancer and autoimmune diseases
  申请人：Tsuji Moriya

  公开号：US20050222048A1

  公开（公告）日：2005-10-06

  The invention is directed to novel compounds of formulae (I), (II) and (III): wherein X is O or NH; R 3 is OH or a monosaccharide and R 4 is hydrogen, or R 3 is hydrogen and R 4 is OH or a monosaccharide; R 5 is hydrogen or a monosaccharide; and pharmaceutically acceptable salts or esters thereof. The invention is also directed to the use of the compounds both directly and as immune adjuvants for treating cancer, infectious diseases and autoimmune diseases. The invention is also directed to syntheses of the intermediates which can be used to make these novel compounds.

  该发明涉及以下化合物的新颖化合物：其中X为O或NH；R3为OH或单糖，R4为氢，或R3为氢，R4为OH或单糖；R5为氢或单糖；以及其药用盐或酯。该发明还涉及这些化合物的直接使用以及作为免疫佐剂用于治疗癌症、传染病和自身免疫疾病。该发明还涉及合成这些中间体的方法，这些中间体可用于制备这些新颖化合物。
• Practical Gram-Scale Synthesis of Either α- or β-Anomer of C-Vinyl Glycosides
  作者：Florian Rouzier、Rosanne Sillé、Arnaud Nourry、Arnaud Tessier、Muriel Pipelier、Stéphane Guillarme

  DOI：10.1055/s-0037-1611800

  日期：2019.6

  Abstract The synthesis C-vinyl glycosides, useful intermediates for the synthesis of C-glycoconjugates, was carried out on gram-scale by controlled reduction of the corresponding ethynyl derivatives in good to excellent yields in different carbohydrate series. The synthesis C-vinyl glycosides, useful intermediates for the synthesis of C-glycoconjugates, was carried out on gram-scale by controlled reduction

  抽象的 合成Ç -乙烯基苷，有用的中间体用于合成Ç -glycoconjugates，通过在良好对应的乙炔基衍生物的受控降低上进行克级在不同的碳水化合物系列优异的产率。 合成Ç -乙烯基苷，有用的中间体用于合成Ç -glycoconjugates，通过在良好对应的乙炔基衍生物的受控降低上进行克级在不同的碳水化合物系列优异的产率。
• Synthesis of Constrained <i>C</i> ‐Glycosyl Amino Acid Derivatives Involving 1,3‐Dipolar Cycloaddition of Cyclic Nitrone as Key Step
  作者：Florian Rouzier、Rosanne Sillé、Ophélie Montiège、Arnaud Tessier、Muriel Pipelier、Gilles Dujardin、Arnaud Martel、Arnaud Nourry、Stéphane Guillarme

  DOI：10.1002/ejoc.202001162

  日期：2020.11.22

  Original conformationally restricted C‐glycosyl amino acid derivatives in different series have been isolated following a two‐step strategy involving 1,3‐dipolar cycloaddition between l‐(–)‐menthone‐derived nitrone and C‐vinylglycosides as the key step. The cycloaddition reaction was highly regio‐ and stereoselective leading to corresponding cycloadducts in high yield. Simple cleavage of the chiral auxiliary

  遵循两步策略，其中一个步骤是分离构象受限的C-糖基氨基酸衍生物，该策略涉及在L -（-）-薄荷酮衍生的硝酮和C-乙烯基糖苷之间进行1,3-偶极环加成，这是关键步骤。环加成反应具有高度的区域选择性和立体选择性，可导致相应的环加合物高产。简单拆分手性助剂可以制备C-糖基氨基酸类似物。
• Glycosyl iodides. History and recent advances
  作者：Peter J. Meloncelli、Alan D. Martin、Todd L. Lowary

  DOI：10.1016/j.carres.2009.02.032

  日期：2009.6

  The use of glycosyl iodides as an effective method for the preparation of glycosides has had a recent resurgence in carbohydrate chemistry, despite its early roots in which these species were believed to be of limited use. Renewed interest in these species as glycosylating agents has been spurred by their demonstrated utility in the stereoselective preparation of O-glycosides, and other glycosylic compounds. This review provides a brief historical account followed by an examination of the use of glycosyl iodides in the synthesis of oligosaccharicles and other glycomimetics, including C-glycosylic compounds, glycosyl azides and N-glycosides. (C) 2009 Elsevier Ltd. All rights reserved.
• Efficient Synthesis of α-C-Galactosyl Ceramide Immunostimulants: Use of Ethylene-Promoted Olefin Cross-Metathesis
  作者：Guangwu Chen、John Schmieg、Moriya Tsuji、Richard W. Franck

  DOI：10.1021/ol0482137

  日期：2004.10.1

  Olefin cross-metathesis has been used to prepare alpha-C-galactosylceramide derivatives. The metathesis process merged vinyl and propenyl glycosides with vinyl derivatives of phytosphingosine. The use of ethylene enhanced the yield of the methathesis step.