O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(benzoyl)-L-serine methyl ester | 698372-49-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(benzoyl)-L-serine methyl ester
• 英文别名: methyl (2S)-2-benzamido-3-[(2R,3R,4R,5R,6R)-3-nitro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropanoate
• CAS: 698372-49-5
• 化学式: C₃₈H₄₀N₂O₁₀
• 分子量: 684.743
• InChiKey: DOPRVNGGIYQBJH-IJAGFNHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  50
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  溶剂黄146 、 O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(benzoyl)-L-serine methyl ester 在 盐酸 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以76%的产率得到O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-N-(benzoyl)-L-serine methyl ester
  参考文献：
  名称：

  2-Nitro Thioglycoside Donors:  Versatile Precursors of β-d-Glycosides of Aminosugars

  摘要：

  2-Nitro thioglycosides can be prepared by the Michael addition of thiophenol to 2-nitroglycal derivatives. NIS/TMSOTf activation of these 2-nitro thioglycosides, in the presence of alcohols, rapidly and cleanly led to the desired glycosides in good yield and beta-selectivity. Reduction of the nitro group allowed generation of the corresponding 2-acetamido glycosides.

  DOI：

  10.1021/ol049729t
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-2-nitro-D-galactal 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 生成 O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(benzoyl)-L-serine methyl ester
  参考文献：
  名称：

  2-Nitro Thioglycoside Donors:  Versatile Precursors of β-d-Glycosides of Aminosugars

  摘要：

  2-Nitro thioglycosides can be prepared by the Michael addition of thiophenol to 2-nitroglycal derivatives. NIS/TMSOTf activation of these 2-nitro thioglycosides, in the presence of alcohols, rapidly and cleanly led to the desired glycosides in good yield and beta-selectivity. Reduction of the nitro group allowed generation of the corresponding 2-acetamido glycosides.

  DOI：

  10.1021/ol049729t

文献信息

• 2-Nitro Thioglycoside Donors:  Versatile Precursors of β-<scp>d</scp>-Glycosides of Aminosugars
  作者：Nadine Barroca、Richard R. Schmidt

  DOI：10.1021/ol049729t

  日期：2004.5.1

  2-Nitro thioglycosides can be prepared by the Michael addition of thiophenol to 2-nitroglycal derivatives. NIS/TMSOTf activation of these 2-nitro thioglycosides, in the presence of alcohols, rapidly and cleanly led to the desired glycosides in good yield and beta-selectivity. Reduction of the nitro group allowed generation of the corresponding 2-acetamido glycosides.