(2R,3R,4S,5S,6R)-2-acetamido-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate | 1385026-80-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,4S,5S,6R)-2-acetamido-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
• 英文别名: N-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)acetamide；[(2R,3S,4S,5R,6R)-6-acetamido-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 1385026-80-1
• 化学式: C₃₆H₃₁NO₁₀
• 分子量: 637.643
• InChiKey: JVNZTVWEJBGKQD-UNKWROQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1-叠氮-1-脱氧-β-D-吡喃半乳糖苷 在 吡啶 、 4-二甲氨基吡啶 、 platinum(IV) oxide 、 氢气 、 caesium carbonate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 16.67h， 生成 (2R,3R,4S,5S,6R)-2-acetamido-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  参考文献：
  名称：

  Synthesis of β-Glycosyl Amides from N-Glycosyl Dinitrobenzenesulfonamides

  摘要：

  The N-glycosyl-2,4-dinitrobenzenesulfonamides were accessed via benzoyl-protected beta-glycosyl azides. The azides were reduced with Adams' catalyst to the corresponding amines. The glycosylamines were sulfonated with 2,4-dinitrobenzenesulfonyl chloride to form N-glycosyl-2,4-dinitrobenzenesulfonamides in moderate yields. beta-Glycosyl amides were then prepared in 67% to 81% yields by treatment of the sulfonamides with thioacetic acid and cesium carbonate. The conversion of the glycosylsulfonamide to the glycosyl amide proceeded with high stereoselectivity.

  DOI：

  10.1080/07328303.2012.663431

文献信息

• Facile and efficient access to C1-aminosugar derivatives under mild conditions
  作者：Mengbi Guo、Xin Wang、Yitong Wang、Zhuang Hou、Chun Guo、Ping Gong

  DOI：10.1016/j.tetlet.2022.153644

  日期：2022.2

  A facile and efficient synthesis of C1-aminosugar derivatives under catalyst-free conditions is described here. In particular, readily available benzoyl glycosyl bromides react smoothly to give a broad scope of C1-aminosugar derivatives in good yields. The present method proves to be efficient and facile in terms of short reaction time, high yield and the broad substrate scope.

  本文描述了在无催化剂条件下简便有效地合成 C1-氨基糖衍生物。特别是，容易获得的苯甲酰溴化糖可以平稳地反应，以良好的收率产生范围广泛的 C1-氨基糖衍生物。本方法在反应时间短、产率高和底物范围广等方面证明是有效和简便的。
• Synthesis of β-Glycosyl Amides from <i>N</i>-Glycosyl Dinitrobenzenesulfonamides
  作者：Vishwanath Gaitonde、Steven J. Sucheck

  DOI：10.1080/07328303.2012.663431

  日期：2012.5.1

  The N-glycosyl-2,4-dinitrobenzenesulfonamides were accessed via benzoyl-protected beta-glycosyl azides. The azides were reduced with Adams' catalyst to the corresponding amines. The glycosylamines were sulfonated with 2,4-dinitrobenzenesulfonyl chloride to form N-glycosyl-2,4-dinitrobenzenesulfonamides in moderate yields. beta-Glycosyl amides were then prepared in 67% to 81% yields by treatment of the sulfonamides with thioacetic acid and cesium carbonate. The conversion of the glycosylsulfonamide to the glycosyl amide proceeded with high stereoselectivity.