(2R,3S,4R,5R,6R)-6-((S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanamido)-5-acetamido-2-(acetoxymethyl)tetrahydro-2H-pyran-3,4-diyl diacetate | 154395-61-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: (2R,3S,4R,5R,6R)-6-((S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanamido)-5-acetamido-2-(acetoxymethyl)tetrahydro-2H-pyran-3,4-diyl diacetate
• 英文别名: N^ω-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-N^α-(9-fluorenylmethyloxycarbonyl))-L-asparagine tert-butyl ester；N-α-fluorenylmethoxycarbonyl-N-γ-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine tert-butyl ester；N-α-fluorenylmethoxycarbonyl-N-β-(2-N-acetylamido-2-deoxy-β-D-glucopyranosyl)-2-tert-butoxy-L-asparagine；tert-butyl (2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoate
• CAS: 154395-61-6
• 化学式: C₃₇H₄₅N₃O₁₃
• 分子量: 739.777
• InChiKey: LCBFPOZEMMSKAF-GBBYZUMQSA-N

物化性质

• 沸点：
  918.2±65.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  53
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  211
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-6-((S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanamido)-5-acetamido-2-(acetoxymethyl)tetrahydro-2H-pyran-3,4-diyl diacetate 在 N,N-二异丙基乙胺 、 fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  Amino acid fluoride for glycopeptide synthesis

  摘要：

  The formation of N-glycosidic linkage between N-acetylglucosamine (GlcNAc) and asparagine (Asn) was effected using aspartic acid gamma-fluoride in combination with either glycosyl azide or silyl carbamate, by the action of Lindlar catalyst or Bu4NF Further elongation of peptide chain was performed to give pentapeptide. This method was further applied into the synthesis of trisaccharidic asparagine, using beta-methoxybenzyl assisted stereoselective B-mannosylation as the key transformation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02228-5
• 作为产物：
  描述：

  [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[(2-methylpropan-2-yl)oxycarbonylamino]oxan-2-yl]methyl acetate 在 2,6-二叔丁基-4-甲基吡啶 、 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 (2R,3S,4R,5R,6R)-6-((S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanamido)-5-acetamido-2-(acetoxymethyl)tetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  Amino acid fluoride for glycopeptide synthesis

  摘要：

  The formation of N-glycosidic linkage between N-acetylglucosamine (GlcNAc) and asparagine (Asn) was effected using aspartic acid gamma-fluoride in combination with either glycosyl azide or silyl carbamate, by the action of Lindlar catalyst or Bu4NF Further elongation of peptide chain was performed to give p