methyl [3,7-anhydro-2-deoxy-3-C-(aminomethyl(N-9-fluorenylmethoxycarbonyl))-D-glycero-L-manno-oct]onate | 903881-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: methyl [3,7-anhydro-2-deoxy-3-C-(aminomethyl(N-9-fluorenylmethoxycarbonyl))-D-glycero-L-manno-oct]onate
• CAS: 903881-99-2
• 化学式: C₂₅H₂₉NO₉
• 分子量: 487.507
• InChiKey: LDSLXVRUNWZUDP-BQYMIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  154.78
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl [3,7-anhydro-2-deoxy-3-C-(aminomethyl(N-9-fluorenylmethoxycarbonyl))-D-glycero-L-manno-oct]onate 以100%的产率得到3,7-anhydro-2-deoxy-3-C-(aminomethyl)-D-glycero-L-manno-octonic acid lactam
  参考文献：
  名称：

  Synthesis of a galacto-configured C-ketoside-based γ-sugar-amino acid and its use in peptide coupling reactions

  摘要：

  gamma-Sugar-amino acid analogues in the form of C-ketosides can be prepared in 5-6 steps starting from D-galactono-1,5-lactone. The key step in the synthesis is the trimethylsilyl trifluoromethanesulfonate (TMSOTf) promoted C-glycosylation of 2-deoxy-3-ulopyranosonates with trimethylsilyl cyanide. Hydrogenation of the resulting beta-cyano esters provides C-ketoside-based gamma-sugar-amino acids that serve as building blocks for the synthesis of unnatural neoglycopeptides. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.006
• 作为产物：
  描述：

  2,3,4,6-四-O-(苯基甲基)-D-半乳糖酸 D-内酯 在 palladium dihydroxide 盐酸 、 三氟甲磺酸三甲基硅酯 、 氢气 、 碳酸氢钠 、 caesium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 105.0h， 生成 methyl [3,7-anhydro-2-deoxy-3-C-(aminomethyl(N-9-fluorenylmethoxycarbonyl))-D-glycero-L-manno-oct]onate
  参考文献：
  名称：

  Synthesis of a galacto-configured C-ketoside-based γ-sugar-amino acid and its use in peptide coupling reactions

  摘要：

  gamma-Sugar-amino acid analogues in the form of C-ketosides can be prepared in 5-6 steps starting from D-galactono-1,5-lactone. The key step in the synthesis is the trimethylsilyl trifluoromethanesulfonate (TMSOTf) promoted C-glycosylation of 2-deoxy-3-ulopyranosonates with trimethylsilyl cyanide. Hydrogenation of the resulting beta-cyano esters provides C-ketoside-based gamma-sugar-amino acids that serve as building blocks for the synthesis of unnatural neoglycopeptides. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.006