allyl 2-O-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-4-O-(2,2,2-trichloroethoxycarbonyl)-3-O-carbamoyl-α-D-galactopyranosiduronamide | 154490-99-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-O-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-4-O-(2,2,2-trichloroethoxycarbonyl)-3-O-carbamoyl-α-D-galactopyranosiduronamide
• 英文别名: allyl 2-O-[2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl]-4-O-(2,2,2-trichloroethoxycarbonyl)-3-O-carbamoyl-α-D-galactopyranosiduronamide；[(2R,3S,4R,5R,6S)-5-acetamido-3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-4-acetyloxy-6-[(2S,3R,4S,5R,6S)-6-carbamoyl-4-carbamoyloxy-2-prop-2-enoxy-5-(2,2,2-trichloroethoxycarbonyloxy)oxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 154490-99-0
• 化学式: C₃₉H₅₃Cl₃N₄O₂₄
• 分子量: 1068.22
• InChiKey: INMNVNWAMGJTGX-PCWDXLAWSA-N

物化性质

• 沸点：
  1131.8±65.0 °C(predicted)
• 密度：
  1.49±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.09
• 重原子数：
  70.0
• 可旋转键数：
  20.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  376.02
• 氢给体数：
  4.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  allyl 2-O-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-4-O-(2,2,2-trichloroethoxycarbonyl)-3-O-carbamoyl-α-D-galactopyranosiduronamide 在 (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 7.5h， 生成 2-O-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-3-O-carbamoyl-4-O-(2,2,2-trichloroethoxycarbonyl)-α-D-galactopyranosiduronamide
  参考文献：
  名称：

  The first synthesis of a moenomycin-type transglycosylase inhibitor

  摘要：

  Starting from chitobiose octaacetate, D-galacturonic acid derivative 3, and D-glyceric acid derived building block 7, the moenomycin trisaccharide analogue 8c has been synthesized. 8c is an as active transglycosylase inhibitor as moenomycin A.

  DOI：

  10.1016/s0040-4020(01)81550-7
• 作为产物：
  描述：

  (3aR)-7c-acetoxy-5c-acetoxymethyl-2-methyl-(3ar,7ac)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-6t-yl tri-O-acetyl-2-acetylamino-β-D-2-deoxy-glucopyranoside 在 camphor-10-sulfonic acid 、 锌 作用下， 以 吡啶 、 甲醇 、 硝基甲烷 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 21.0h， 生成 allyl 2-O-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-4-O-(2,2,2-trichloroethoxycarbonyl)-3-O-carbamoyl-α-D-galactopyranosiduronamide
  参考文献：
  名称：

  The first synthesis of a moenomycin-type transglycosylase inhibitor

  摘要：

  Starting from chitobiose octaacetate, D-galacturonic acid derivative 3, and D-glyceric acid derived building block 7, the moenomycin trisaccharide analogue 8c has been synthesized. 8c is an as active transglycosylase inhibitor as moenomycin A.

  DOI：

  10.1016/s0040-4020(01)81550-7