3-azidopropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside | 595569-05-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-azidopropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS: 595569-05-4
• 化学式: C₃₉H₅₀N₄O₁₅
• 分子量: 814.844
• InChiKey: QIEUOWICJKOUMZ-ZTFBNPIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  58.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  238.44
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  3-azidopropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 3-azidopropyl β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of the sialyl-α-(2→3′)-lactosamine trisaccharide with a 3-aminopropyl group as a spacer at the reducing end

  摘要：

  The trisaccharide, 3-aminopropyl 5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto -2-nonulopyranosylonic acid-(2 --> 3)-beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside has been synthesized chemoenzymatically for the first time. First, the acceptor, 3-aminopropyl beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside was synthesized in a conventional chemical manner, and then it was coupled with CMP-sialic acid using alpha-(2 --> 3)-(N)-sialyltransferase to afford the desired trisaccharide by an enzymatically stereocontrolled manner. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00167-8
• 作为产物：
  描述：

  3-azidopropyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 sodium hydroxide 、 四丁基溴化铵 、 sodium methylate 、 silver trifluoromethanesulfonate 、 二正丁基氧化锡 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 120.0h， 生成 3-azidopropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of the sialyl-α-(2→3′)-lactosamine trisaccharide with a 3-aminopropyl group as a spacer at the reducing end

  摘要：

  The trisaccharide, 3-aminopropyl 5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto -2-nonulopyranosylonic acid-(2 --> 3)-beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside has been synthesized chemoenzymatically for the first time. First, the acceptor, 3-aminopropyl beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside was synthesized in a conventional chemical manner, and then it was coupled with CMP-sialic acid using alpha-(2 --> 3)-(N)-sialyltransferase to afford the desired trisaccharide by an enzymatically stereocontrolled manner. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00167-8