propyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-2-acetamido-2-deoxy-β-D-galactopyranoside | 114661-03-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: propyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-2-acetamido-2-deoxy-β-D-galactopyranoside
• CAS: 114661-03-9
• 化学式: C₂₂H₃₈N₂O₁₄
• 分子量: 554.549
• InChiKey: PVHAUCUYKGSTIQ-KKWQASKRSA-N

物化性质

• 沸点：
  982.3±65.0 °C(predicted)
• 密度：
  1.50±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.47
• 重原子数：
  38.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  253.8
• 氢给体数：
  9.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  allyl 2-azido-2-deoxy-β-D-galactopyranoside 在 palladium on activated charcoal sodium hydroxide 、 molecular sives 4A 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 为溶剂， 反应 36.0h， 生成 propyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-2-acetamido-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Total synthesis of 3-O-[2-acetamido-6-O-(N-acetyl-α-d-neuraminyl)-2-deoxy-α-d-galactosyl]-l-serine and a stereoisomer

  摘要：

  O-(5-Acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2- nonulopyranoxylonic acid)-(2----6)-O-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-(1----3) -L-serine, a structural unit occurring in various submaxillary mucins, was synthesized for the first time by using O-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D- galacto-2-nonulopyranosyl)onate]-(2----6)-3,4-di-O-acetyl-2- azido-2-deoxy-D- galactopyranosyl trichloroacetimidate (13) and N-(benzyloxycarbonyl)-L-serine benzyl ester as the key intermediates. The trichloroacetimidate 13 was prepared by starting from two monosaccharide synthons, namely, allyl 2-azido-2-deoxy-beta-D-galactopyranoside and methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-beta-D- galacto-2-nonulopyranosyl chloride)onate, which were coupled in the presence of silver triflate in tetrahydrofuran to give the desired alpha-(2----6)-linked disaccharide in moderate selectivity.

  DOI：

  10.1016/s0008-6215(00)90853-x