Methyl (ethyl 3,4-di-O-benzyl-1-thio-β-D-glucopyranosid)uronate | 162613-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl (ethyl 3,4-di-O-benzyl-1-thio-β-D-glucopyranosid)uronate
• 英文别名: methyl (ethyl 3,4-di-O-benzyl-1-thio-β-D-glucopyranosyl)uronate；methyl (2S,3S,4R,5R,6S)-6-ethylsulfanyl-5-hydroxy-3,4-bis(phenylmethoxy)oxane-2-carboxylate
• CAS: 162613-17-4
• 化学式: C₂₃H₂₈O₆S
• 分子量: 432.538
• InChiKey: YAZFIPBSHFHFIB-RBRWEJTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  99.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl (ethyl 3,4-di-O-benzyl-1-thio-β-D-glucopyranosid)uronate 在 吡啶 、 4 A molecular sieve 、 DMTST 作用下， 以 二氯甲烷 为溶剂， 反应 144.0h， 生成 methyl (2S,3S,4S,5R,6R)-6-[[(2R,4aR,6S,7S,8S,8aR)-6-methoxy-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]oxy]-5-(2,2-dimethylpropanoyloxy)-3,4-bis(phenylmethoxy)oxane-2-carboxylate
  参考文献：
  名称：

  Synthesis of Methyl (Ethyl 2-O-acyl-3,4-di-O-benzyl-1-thio-.beta.-D-glucopyranosid)uronates and Evaluation of Their Use as Reactive .beta.-Selective Glucuronic Acid Donors

  摘要：

  The synthesis of derivatives of methyl (ethyl 2-0-acyl-3,4-di-O-benzyl-1-thio-beta-D-glucopyranosid)-uronate with different ester groups (acetyl, benzoyl, pivaloyl, and anisoyl) at O-2 is described. The synthesis proceeds via a two-step oxidation (DMSO/DCC followed by PDC/MeOH) of C-6 on a suitably protected glucose derivative to give directly the methyl glucuronic ester without affecting the thioglycoside. The thioglucuronides were tested as donors in coupling reactions with unreactive carbohydrate alcohols using dimethyl(methylthio)sulfonium triflate (DMTST) as promoter, Due to the activating benzyl protecting groups at O-3 and -4, the sluggishness of fully acylated glucuronic acid donors could be overcome and glucuronide disaccharides were produced in fair to good yields. The glucuronides were obtained with the desired P-configuration because of the participating group at O-2. Among the different ester groups tried, the benzoyl group was found to give the highest yield in the couplings.

  DOI：

  10.1021/jo00112a046
• 作为产物：
  描述：

  ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 吡啶 、 重铬酸吡啶 、 三氯化铝 、 硼烷-三甲胺络合物 、 4 A molecular sieve 、 sodium methylate 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 Methyl (ethyl 3,4-di-O-benzyl-1-thio-β-D-glucopyranosid)uronate
  参考文献：
  名称：

  Synthesis of Methyl (Ethyl 2-O-acyl-3,4-di-O-benzyl-1-thio-.beta.-D-glucopyranosid)uronates and Evaluation of Their Use as Reactive .beta.-Selective Glucuronic Acid Donors

  摘要：

  The synthesis of derivatives of methyl (ethyl 2-0-acyl-3,4-di-O-benzyl-1-thio-beta-D-glucopyranosid)-uronate with different ester groups (acetyl, benzoyl, pivaloyl, and anisoyl) at O-2 is described. The synthesis proceeds via a two-step oxidation (DMSO/DCC followed by PDC/MeOH) of C-6 on a suitably protected glucose derivative to give directly the methyl glucuronic ester without affecting the thioglycoside. The thioglucuronides were tested as donors in coupling reactions with unreactive carbohydrate alcohols using dimethyl(methylthio)sulfonium triflate (DMTST) as promoter, Due to the activating benzyl protecting groups at O-3 and -4, the sluggishness of fully acylated glucuronic acid donors could be overcome and glucuronide disaccharides were produced in fair to good yields. The glucuronides were obtained with the desired P-configuration because of the participating group at O-2. Among the different ester groups tried, the benzoyl group was found to give the highest yield in the couplings.

  DOI：

  10.1021/jo00112a046

文献信息

• Total Syntheses of Conjugation‐Ready Repeating Units of<i>Acinetobacter baumannii</i>AB5075 for Glycoconjugate Vaccine Development
  作者：Shuo Zhang、Peter H. Seeberger

  DOI：10.1002/chem.202103234

  日期：2021.12.9

  the repeating unit of A. baumannii AB5075 as well as two analogues containing a challenging (S)-3-hydroxybutanoyl chain were synthesized. All of the oligosaccharides bear an amino group that allows for the covalent attachment to glycan microarrays and carrier proteins. These densely functionalized aminoglycoside trisaccharides are the basis for the development of novel glycoconjugate vaccines against

  使用高效和立体选择性的糖基化和双序列倒置策略，合成了鲍曼不动杆菌AB5075 的重复单元以及含有具有挑战性的 ( S )-3-羟基丁酰基链的两个类似物。所有寡糖都带有氨基，可以共价连接到聚糖微阵列和载体蛋白上。这些密集功能化的氨基糖苷三糖是开发针对鲍曼不动杆菌的新型糖复合物疫苗的基础。
• Synthesis of Methyl (Ethyl 2-O-acyl-3,4-di-O-benzyl-1-thio-.beta.-D-glucopyranosid)uronates and Evaluation of Their Use as Reactive .beta.-Selective Glucuronic Acid Donors
  作者：Per J. Garegg、Lars Olsson、Stefan Oscarson

  DOI：10.1021/jo00112a046

  日期：1995.4

  The synthesis of derivatives of methyl (ethyl 2-0-acyl-3,4-di-O-benzyl-1-thio-beta-D-glucopyranosid)-uronate with different ester groups (acetyl, benzoyl, pivaloyl, and anisoyl) at O-2 is described. The synthesis proceeds via a two-step oxidation (DMSO/DCC followed by PDC/MeOH) of C-6 on a suitably protected glucose derivative to give directly the methyl glucuronic ester without affecting the thioglycoside. The thioglucuronides were tested as donors in coupling reactions with unreactive carbohydrate alcohols using dimethyl(methylthio)sulfonium triflate (DMTST) as promoter, Due to the activating benzyl protecting groups at O-3 and -4, the sluggishness of fully acylated glucuronic acid donors could be overcome and glucuronide disaccharides were produced in fair to good yields. The glucuronides were obtained with the desired P-configuration because of the participating group at O-2. Among the different ester groups tried, the benzoyl group was found to give the highest yield in the couplings.