N4-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-malamic acid chloralid | 320741-20-6

• 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: N4-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-malamic acid chloralid
• 英文别名: N⁴-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-malamic acid chloralid
• CAS: 320741-20-6
• 化学式: C₂₀H₂₅Cl₃N₂O₁₂
• 分子量: 591.784
• InChiKey: UPAMYWMQPZTTIN-PYPPLNBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.21
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  181.86
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N4-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-malamic acid chloralid 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以38%的产率得到N⁴-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-2-hydroxysuccinamide
  参考文献：
  名称：

  Synthesis of N4-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-asparagine analogues: Succinamide, l-2-hydroxysuccinamide, and l-2-hydroxysuccinamic acid hydrazide analogues

  摘要：

  The syntheses of three analogues of N-4-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)-L-asparagine are described. N-(2-Acetamido-2-deoxy-beta -D-glucopyranosyl)succinamide wa a synthesized by the reaction of pentafluorophenyl succinamate with 2-acetamido-2-deoxy-beta -D-glucopyranosylamine. 2-Acetamido-3,4, 6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosylamine was synthesized, and the complete assignment of the H-1 NMR spectrum is given. Reaction of the protected beta -D-glycosylamine with L-malic acid chloralid in the presence of a coupling agent (EEDQ) gave N-4-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl)-L-malamic acid chloralid that was deprotected two ways: (1) using ammonia, which gave N4-(2-acetamido-2-deoxy-betaw-D-glucopyranosyl)-L-2-hydroxysuccinamide, and (2) using hydrazine, which gave N-4-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)- L-2-hydroxysuccinamic acid hydratide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00224-x
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-Β-D-吡喃葡萄糖酰基叠氮化物 在 platinum(IV) oxide 氢气 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 22.0h， 生成 N4-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-malamic acid chloralid
  参考文献：
  名称：

  Synthesis of N4-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-asparagine analogues: Succinamide, l-2-hydroxysuccinamide, and l-2-hydroxysuccinamic acid hydrazide analogues

  摘要：

  The syntheses of three analogues of N-4-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)-L-asparagine are described. N-(2-Acetamido-2-deoxy-beta -D-glucopyranosyl)succinamide wa a synthesized by the reaction of pentafluorophenyl succinamate with 2-acetamido-2-deoxy-beta -D-glucopyranosylamine. 2-Acetamido-3,4, 6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosylamine was synthesized, and the complete assignment of the H-1 NMR spectrum is given. Reaction of the protected beta -D-glycosylamine with L-malic acid chloralid in the presence of a coupling agent (EEDQ) gave N-4-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl)-L-malamic acid chloralid that was deprotected two ways: (1) using ammonia, which gave N4-(2-acetamido-2-deoxy-betaw-D-glucopyranosyl)-L-2-hydroxysuccinamide, and (2) using hydrazine, which gave N-4-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)- L-2-hydroxysuccinamic acid hydratide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00224-x