2-acetamido-3,6-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-α-D-glucopyranosyl chloride | 849501-64-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 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-glucopyranosyl chloride
• 英文别名: [(2R,3S,4S,5R,6S)-6-[(2R,3S,4R,5R,6R)-5-acetamido-4-benzoyloxy-2-(benzoyloxymethyl)-6-chlorooxan-3-yl]oxy-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 849501-64-0
• 化学式: C₅₆H₄₈ClNO₁₆
• 分子量: 1026.45
• InChiKey: XSBUZVSQMQOJRO-WAZYJCAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  74
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  215
• 氢给体数：
  1
• 氢受体数：
  16

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-glucopyranosyl chloride 在 3 A molecular sieve 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以84%的产率得到[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-(benzoyloximino)-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-arabino-hexopyranosyl bromide 在 氯化亚砜 、 ammonium cerium(IV) nitrate 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 40.0h， 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-glucopyranosyl chloride
  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

文献信息

• Alternative Access to Lactosamine-derived Oxazoline via 2-Ulose Oxime as a Key Intermediate
  作者：Eisuke Kaji、Yumiko Osa、Naomi Shinohara、Chiho Yanagi、Masae Sekine、Takashi Nishino

  DOI：10.3987/com-04-s(p)28

  日期：——

  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.