3,7-anhydro-2-deoxy-3-C-(aminomethyl(N-9-fluorenylmethoxycarbonyl))-D-glycero-L-manno-octonic acid | 903881-96-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 3,7-anhydro-2-deoxy-3-C-(aminomethyl(N-9-fluorenylmethoxycarbonyl))-D-glycero-L-manno-octonic acid
• 英文别名: 2-[(2R,3R,4S,5R,6R)-2-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]acetic acid
• CAS: 903881-96-9
• 化学式: C₂₄H₂₇NO₉
• 分子量: 473.48
• InChiKey: RCAQRBWRKVYVKV-DXRYYMCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,7-anhydro-2-deoxy-3-C-(aminomethyl(N-9-fluorenylmethoxycarbonyl))-D-glycero-L-manno-octonic acid 在 吗啉 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 63.0h， 生成 3,7-anhydro-2-deoxy-3-C-(aminomethyl(N-L-Phe-N^α(Fmoc)amide))-D-glycero-L-manno-octon-(L-Ala-OMe)amide
  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：

  benzyl (4,5,6,8-tetra-O-benzyl-2-deoxy-α-D-galacto-3-octulopyranosid)onate 在 palladium dihydroxide 盐酸 、 三氟甲磺酸三甲基硅酯 、 氢气 作用下， 以 甲醇 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 96.0h， 生成 3,7-anhydro-2-deoxy-3-C-(aminomethyl(N-9-fluorenylmethoxycarbonyl))-D-glycero-L-manno-octonic acid
  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

文献信息

• Synthesis of a galacto-configured C-ketoside-based γ-sugar-amino acid and its use in peptide coupling reactions
  作者：Frank Schweizer、Ole Hindsgaul

  DOI：10.1016/j.carres.2006.03.006

  日期：2006.7

  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.