tert-butyl (3S)-4-[[1-[(2R,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-methoxyoxan-3-yl]triazol-4-yl]methylamino]-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoate | 1110650-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl (3S)-4-[[1-[(2R,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-methoxyoxan-3-yl]triazol-4-yl]methylamino]-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoate
• CAS: 1110650-08-2
• 化学式: C₃₉H₄₇N₅O₁₃
• 分子量: 793.828
• InChiKey: SQKNVLRPFMQDCM-BGJYJLNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  57
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  222
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S)-4-[[1-[(2R,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-methoxyoxan-3-yl]triazol-4-yl]methylamino]-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoate 、 五氟苯酚 在 三氟乙酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 17.0h， 以74%的产率得到(2,3,4,5,6-pentafluorophenyl) (3S)-4-[[1-[(2R,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-methoxyoxan-3-yl]triazol-4-yl]methylamino]-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoate
  参考文献：
  名称：

  Preparation of Some Glycosyl Amino Acid Building Blocks via Click Reaction and Construction of a Glycotetrapeptide Library Using Spot Synthesis

  摘要：

  The copper-catalyzed 1,3-dipolar cycloaddition reaction between ethyl 2,3,4-tri-O- actetyl-6-azido-6-deoxy-1-thio-beta-D-glucopyranoside (2), ethyl 2,3,4-tri-O-actetyl-6-azido-6-deoxy-1-thio-beta-D-galactopyranoside (4), methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-alpha-D-mannopyranoside (7), and methyl 2,3,6-tri-O-acetyl-2-azido-2-deoxy-beta-D-glucopyranoside (9), and tert-butyl-protected Fmoc-asparaginic acid propargylamide (10) gave the corresponding protected glycosyl amino acid building blocks 11, 13, 15, and 17 in 67% to 95% yield. The latter were converted into the corresponding pentafluorophenyl esters 12, 14, 16, and 18, which were used for a spot synthesis of a combinatorial library containing 256 glycotetrapeptides. The library was screened for lectin-binding affinity with the lectins Concanavalin A (Con A), phaseolus vulgaris (PHA-E), and galantus nivalis (GNA).

  DOI：

  10.1080/07328300802419873
• 作为产物：
  描述：

  tert-butyl N²-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-prop-2-yn-1-yl-L-asparaginate 、 methyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside 在 3P(OC₂H₅)3*Cu⁽¹⁺⁾*I^(1-)=[P(OC₂H₅)3]3CuI 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以84%的产率得到tert-butyl (3S)-4-[[1-[(2R,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-methoxyoxan-3-yl]triazol-4-yl]methylamino]-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoate
  参考文献：
  名称：

  Preparation of Some Glycosyl Amino Acid Building Blocks via Click Reaction and Construction of a Glycotetrapeptide Library Using Spot Synthesis

  摘要：

  The copper-catalyzed 1,3-dipolar cycloaddition reaction between ethyl 2,3,4-tri-O- actetyl-6-azido-6-deoxy-1-thio-beta-D-glucopyranoside (2), ethyl 2,3,4-tri-O-actetyl-6-azido-6-deoxy-1-thio-beta-D-galactopyranoside (4), methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-alpha-D-mannopyranoside (7), and methyl 2,3,6-tri-O-acetyl-2-azido-2-deoxy-beta-D-glucopyranoside (9), and tert-butyl-protected Fmoc-asparaginic acid propargylamide (10) gave the corresponding protected glycosyl amino acid building blocks 11, 13, 15, and 17 in 67% to 95% yield. The latter were converted into the corresponding pentafluorophenyl esters 12, 14, 16, and 18, which were used for a spot synthesis of a combinatorial library containing 256 glycotetrapeptides. The library was screened for lectin-binding affinity with the lectins Concanavalin A (Con A), phaseolus vulgaris (PHA-E), and galantus nivalis (GNA).

  DOI：

  10.1080/07328300802419873