propyl O--(2->6)-2-acetamido-3,4-di-O-acetyl-2-deoxy-β-D-galactopyranoside | 116246-49-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: propyl O--(2->6)-2-acetamido-3,4-di-O-acetyl-2-deoxy-β-D-galactopyranoside
• CAS: 116246-49-2
• 化学式: C₃₅H₅₂N₂O₂₀
• 分子量: 820.799
• InChiKey: XDUJARZYNINKAA-CEWRNWBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.96
• 重原子数：
  57.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  279.22
• 氢给体数：
  2.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  propyl O--(2->6)-2-acetamido-3,4-di-O-acetyl-2-deoxy-β-D-galactopyranoside 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 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
• 作为产物：
  描述：

  allyl 2-azido-2-deoxy-β-D-galactopyranoside 在 palladium on activated charcoal molecular sives 4A 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 为溶剂， 反应 33.0h， 生成 propyl O--(2->6)-2-acetamido-3,4-di-O-acetyl-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