2-acetamido-3,6-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-α-D-glucopyranose | 849501-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-3,6-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-α-D-glucopyranose
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Gal(b1-4)[Bz(-3)][Bz(-6)]a-GlcNAc；[(2R,3S,4R,5R,6S)-5-acetamido-4-benzoyloxy-6-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 849501-74-2
• 化学式: C₅₆H₄₉NO₁₇
• 分子量: 1008.0
• InChiKey: GQOCTQLPAKUBQT-PEFDOSKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  74.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  234.82
• 氢给体数：
  2.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  2-acetamido-3,6-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-α-D-glucopyranose 在 氯化亚砜 、 3 A molecular sieve 、 silver trifluoromethanesulfonate 、 N,N-二甲基甲酰胺 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 [4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3,6-di-O-benzoyl-D-glucopyrano]-2-methyl-[2,1-d]-2-oxazoline
  参考文献：
  名称：

  Alternative Access to Lactosamine-derived Oxazoline via 2-Ulose Oxime as a Key Intermediate

  摘要：

  Lactosamine-derived oxazoline was synthesized via 2-ulose oxime as a key intermediate, in which substituent effects of the acyloxyimino group were investigated. On reduction of the oxime to amino group, p-chlorobenzoyloxime provided a good gluco : manno selectivity of 13 : 1. N-Acetyllactosaminyl chloride derived therefrom was readily converted into the oxazoline by AgOTf-promoted cyclization with an 84% yield.

  DOI：

  10.3987/com-04-s(p)28
• 作为产物：
  描述：

  3,6-di-O-benzoyl-2-(p-chlorobenzoyloxyimino)-2-deoxy-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-arabino-hexopyranosyl bromide 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 20.0h， 生成 2-acetamido-3,6-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-α-D-glucopyranose
  参考文献：
  名称：

  Alternative Access to Lactosamine-derived Oxazoline via 2-Ulose Oxime as a Key Intermediate

  摘要：

  Lactosamine-derived oxazoline was synthesized via 2-ulose oxime as a key intermediate, in which substituent effects of the acyloxyimino group were investigated. On reduction of the oxime to amino group, p-chlorobenzoyloxime provided a good gluco : manno selectivity of 13 : 1. N-Acetyllactosaminyl chloride derived therefrom was readily converted into the oxazoline by AgOTf-promoted cyclization with an 84% yield.

  DOI：

  10.3987/com-04-s(p)28