2-(trimethylsilyl)ethyl (3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-(1->6)-(3,4-di-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranoside) | 698371-81-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl (3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-(1->6)-(3,4-di-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranoside)
• 英文别名: trimethyl-[2-[(2S,3R,4R,5R,6R)-3-nitro-6-[[(2R,3R,4R,5R,6R)-3-nitro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]-4,5-bis(phenylmethoxy)oxan-2-yl]oxyethyl]silane
• CAS: 698371-81-2
• 化学式: C₅₂H₆₂N₂O₁₃Si
• 分子量: 951.155
• InChiKey: KXEXTEIIRWBILX-CMVQBLQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.66
• 重原子数：
  68
• 可旋转键数：
  23
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  175
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  溶剂黄146 、 2-(trimethylsilyl)ethyl (3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-(1->6)-(3,4-di-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranoside) 在 盐酸 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以60%的产率得到2-(trimethylsilyl)ethyl (2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->6)-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranoside)
  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：

  2-(trimethylsilyl)ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 三氟化硼乙醚 、 乙酸酐 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.33h， 生成 2-(trimethylsilyl)ethyl (3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-(1->6)-(3,4-di-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranoside)
  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.