methyl 5-acetamido-3-bromo-2-(dibenzylphosphoryl)-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate | 153658-76-5

• 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: methyl 5-acetamido-3-bromo-2-(dibenzylphosphoryl)-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate
• 英文别名: Methyl 3-bromo-5-acetamido-4,7,8,9-tetra-O-acetyl-2-O-(dibenzylphosphityl)-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate；methyl (2S,3R,4R,5S,6R)-5-acetamido-4-acetyloxy-2-bis(phenylmethoxy)phosphanyloxy-3-bromo-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 153658-76-5
• 化学式: C₃₄H₄₁BrNO₁₅P
• 分子量: 814.575
• InChiKey: ZTYBECBZOWSWLQ-JYWVFQTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  52
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-3-bromo-2-(dibenzylphosphoryl)-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以43%的产率得到methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-O-dibenzyloxyphosphoryl-3,5-dideoxy-β-D-glycero-D-galacto-non-2-ulopyranosonate
  参考文献：
  名称：

  Sim, Mui Mui; Kondo, Hirosato; Wong, Chi-Huey, Journal of the American Chemical Society, 1993, vol. 115, # 6, p. 2260 - 2267

  摘要：

  DOI：
• 作为产物：
  描述：

  二苄基二乙基胺基膦 、 Methyl 3-bromo-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate 在 1H-1,2,4-三唑 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以88%的产率得到methyl 5-acetamido-3-bromo-2-(dibenzylphosphoryl)-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate
  参考文献：
  名称：

  Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism

  摘要：

  The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and accepters for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides. Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed. When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH. The glycosyl phosphite can also be activated by TMSOTf directly. The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.

  DOI：

  10.1021/jo00083a032