[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[(2-methylpropan-2-yl)oxycarbonylamino]oxan-2-yl]methyl acetate | 267432-02-0

• 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: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[(2-methylpropan-2-yl)oxycarbonylamino]oxan-2-yl]methyl acetate
• CAS: 267432-02-0
• 化学式: C₁₉H₃₀N₂O₁₀
• 分子量: 446.455
• InChiKey: DAUPWKYEBOJOEH-WRQOLXDDSA-N

物化性质

• 沸点：
  598.0±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  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 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：

  二碳酸二叔丁酯 、 2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-Β-D-吡喃葡萄糖酰基叠氮化物 在 Lindlar's catalyst 氢气 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以87%的产率得到[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[(2-methylpropan-2-yl)oxycarbonylamino]oxan-2-yl]methyl acetate
  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