methyl (phenyl 4-O-acetyl-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate) | 1319717-06-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (phenyl 4-O-acetyl-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)
• 英文别名: methyl (2S,3S,4R,5S,6S)-3-acetyloxy-4,5-diazido-6-phenylsulfanyloxane-2-carboxylate
• CAS: 1319717-06-0
• 化学式: C₁₅H₁₆N₆O₅S
• 分子量: 392.395
• InChiKey: LYWHSSPIAGMUCU-MCZMQQNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl (phenyl 4-O-acetyl-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate) 在 三叔丁基膦 、 二苯基亚砜 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.83h， 生成 p-methoxyphenyl 3-O-(methyl 4-O-acetyl-2,3-diazido-2,3-dideoxy-β-D-mannopyranosyl uronate)-2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 、 p-methoxyphenyl 3-O-(methyl 4-O-acetyl-2,3-diazido-2,3-dideoxy-α-D-mannopyranosyl uronate)-2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of 2,3-Diamino-2,3-dideoxy-β-d-mannopyranosyl Uronates

  摘要：

  With the aim to find an efficient synthetic procedure for the construction of 2,3-diamino-2,3-dideoxy-beta-D-mannuronic acids, we evaluated three mannosyl donors: (S)-phenyl 4,6-di-O-acetyl-2,3-diazido mannopyranoside, (S)-phenyl 2,3-diazido-4,6-O-benzylidene mannopyranoside, and (S)-phenyl 2,3-diazido mannopyranosyl methyl uronate. The first two mannosylating agents are rather unselective or slightly a-selective in their condensation with three different acceptors. The mannuronic acid donor on the other hand reliably provides the desired beta-mannosidic linkage. A mechanistic rationale is put forward to account for the different behavior of the three donor types. Suitably protected 2,3-diazido mannuronic acids were employed to construct the all-cis-linked tetrasaccharide repeating unit of the capsular polysaccharide of Bacillus stearothermophilus, featuring two 2,3-diacetamido-2,3-dideoxy-beta-D-mannuronic acids.

  DOI：

  10.1021/jo201179p
• 作为产物：
  描述：

  acetyl 4,6-di-O-acetyl-2,3-diazido-2,3-dideoxy-D-mannopyranoside 在 吡啶 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 三氟化硼乙醚 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 methyl (phenyl 4-O-acetyl-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)
  参考文献：
  名称：

  Stereoselective Synthesis of 2,3-Diamino-2,3-dideoxy-β-d-mannopyranosyl Uronates

  摘要：

  With the aim to find an efficient synthetic procedure for the construction of 2,3-diamino-2,3-dideoxy-beta-D-mannuronic acids, we evaluated three mannosyl donors: (S)-phenyl 4,6-di-O-acetyl-2,3-diazido mannopyranoside, (S)-phenyl 2,3-diazido-4,6-O-benzylidene mannopyranoside, and (S)-phenyl 2,3-diazido mannopyranosyl methyl uronate. The first two mannosylating agents are rather unselective or slightly a-selective in their condensation with three different acceptors. The mannuronic acid donor on the other hand reliably provides the desired beta-mannosidic linkage. A mechanistic rationale is put forward to account for the different behavior of the three donor types. Suitably protected 2,3-diazido mannuronic acids were employed to construct the all-cis-linked tetrasaccharide repeating unit of the capsular polysaccharide of Bacillus stearothermophilus, featuring two 2,3-diacetamido-2,3-dideoxy-beta-D-mannuronic acids.

  DOI：

  10.1021/jo201179p

文献信息

• Mannopyranosyl Uronic Acid Donor Reactivity
  作者：Marthe T. C. Walvoort、Wilbert de Witte、Jesse van Dijk、Jasper Dinkelaar、Gerrit Lodder、Herman S. Overkleeft、Jeroen D. C. Codée、Gijsbert A. van der Marel

  DOI：10.1021/ol2016862

  日期：2011.8.19

  The reactivity of a variety of mannopyranosyl uronic acid donors was assessed In a set of competition experiments, in which two (S)-tolyl mannosyl donors were made to compete for a limited amount of promoter (NIS/TfOH). These experiments revealed that the reactivity of mannuronic acid donors is significantly higher than expected based on the electron-withdrawing capacity of the C-5 carboxylic acid ester function. A 4-O-acetyl-beta-(S)-tolyl mannuronic acid donor was found to have similar reactivity as per-O-benzyl-alpha-(S)-tolyl mannose.