phenyl 4-O-benzyl-3,6-di-O-dimethylthexylsilyl-2-deoxy-2-nitro-1-thio-β-D-galactopyranoside | 698371-33-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4-O-benzyl-3,6-di-O-dimethylthexylsilyl-2-deoxy-2-nitro-1-thio-β-D-galactopyranoside
• 英文别名: 2,3-dimethylbutan-2-yl-[(2R,3S,4R,5R,6S)-2-[[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxymethyl]-5-nitro-3-phenylmethoxy-6-phenylsulfanyloxan-4-yl]oxy-dimethylsilane
• CAS: 698371-33-4
• 化学式: C₃₅H₅₇NO₆SSi₂
• 分子量: 676.078
• InChiKey: QWYCGAQHSJMYHA-AALIFHQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.42
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 phenyl 4-O-benzyl-3,6-di-O-dimethylthexylsilyl-2-deoxy-2-nitro-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 以68%的产率得到methyl 4-O-benzyl-3,6-di-O-dimethylthexylsilyl-2-deoxy-2-nitro-β-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：

  苯硫酚 、 1,5-anhydro-4-O-benzyl-3,6-di-O-dimethylthexylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 以88%的产率得到phenyl 4-O-benzyl-3,6-di-O-dimethylthexylsilyl-2-deoxy-2-nitro-1-thio-β-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.