7-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-4-methylcoumarin | 460085-43-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-4-methylcoumarin
• 英文别名: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-azido-6-(4-methyl-2-oxochromen-7-yl)oxyoxan-2-yl]methyl acetate
• CAS: 460085-43-2
• 化学式: C₂₂H₂₃N₃O₁₀
• 分子量: 489.439
• InChiKey: NUCMFNFBECGZSA-FYKMYLNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  7-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-4-methylcoumarin 在 苯硫酚 、 三乙胺 、 tin(ll) chloride 作用下， 以 乙腈 为溶剂， 生成 [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-amino-6-(4-methyl-2-oxochromen-7-yl)oxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of 7-O-(2-deoxy-2-sulfamido-α-d-glucopyranosyl)-4-methylcoumarin sodium salt: a fluorogenic substrate for sulfamidase

  摘要：

  The title compound, useful for testing the efficacy of heparin sulfamidase, was synthesized in good yield starting from 2-azido-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranosyl fluoride, reducing the azido group efficiently with SnCl2-PhSH-Et3N reagent and finally crystallizing the N-sulfated product from methanol after deacetylation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00088-5
• 作为产物：
  描述：

  羟甲香豆素 在 吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 7-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-4-methylcoumarin
  参考文献：
  名称：

  Synthesis of 7-O-(2-deoxy-2-sulfamido-α-d-glucopyranosyl)-4-methylcoumarin sodium salt: a fluorogenic substrate for sulfamidase

  摘要：

  The title compound, useful for testing the efficacy of heparin sulfamidase, was synthesized in good yield starting from 2-azido-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranosyl fluoride, reducing the azido group efficiently with SnCl2-PhSH-Et3N reagent and finally crystallizing the N-sulfated product from methanol after deacetylation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00088-5

文献信息

• SZWEDA, R.;SPOHR, U.;LEMIEUX, R. U.;SCHINDLER, D.;BISHOP, D. F.;DESNICK, +, CAN. J. CHEM., 67,(1989) N, C. 1388-1391
  作者：SZWEDA, R.、SPOHR, U.、LEMIEUX, R. U.、SCHINDLER, D.、BISHOP, D. F.、DESNICK, +

  DOI：——

  日期：——