N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-((2R,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-L-cysteine | 1533407-93-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-((2R,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-L-cysteine
• CAS: 1533407-93-0
• 化学式: C₂₆H₃₀N₂O₉S
• 分子量: 546.598
• InChiKey: WUNPRCHENDWPJU-SYQKRSDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  174.65
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-((2R,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-L-cysteine 在 哌啶 、 吗啉 、 吡啶 、 四(三苯基膦)钯 、 caesium carbonate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.58h， 生成 Ac-L-Cys(α-D-(OAc)3GalNAc)-NHMe
  参考文献：
  名称：

  S-Michael Additions to Chiral Dehydroalanines as an Entry to Glycosylated Cysteines and a Sulfa-Tn Antigen Mimic

  摘要：

  Stereoselective sulfa-Michael addition of appropriately protected thiocarbohydrates to chiral dehydroalanines has been developed as a key step in the synthesis of biologically important cysteine derivatives, such as S-(beta-D-glucopyranosyl)-D-cysteine, which has not been synthesized to date, and S-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-L-cysteine, which could be considered as a mimic of Tn antigen. The corresponding diamide derivative was also synthesized and analyzed from a conformational viewpoint, and its bound state with a lectin was studied.

  DOI：

  10.1021/ja411522f
• 作为产物：
  描述：

  S-(2-acetamido-2-deoxy-α-D-galactosyl)-L-cysteine hydrochloride 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 以73%的产率得到N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-((2R,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-L-cysteine
  参考文献：
  名称：

  S-Michael Additions to Chiral Dehydroalanines as an Entry to Glycosylated Cysteines and a Sulfa-Tn Antigen Mimic

  摘要：

  Stereoselective sulfa-Michael addition of appropriately protected thiocarbohydrates to chiral dehydroalanines has been developed as a key step in the synthesis of biologically important cysteine derivatives, such as S-(beta-D-glucopyranosyl)-D-cysteine, which has not been synthesized to date, and S-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-L-cysteine, which could be considered as a mimic of Tn antigen. The corresponding diamide derivative was also synthesized and analyzed from a conformational viewpoint, and its bound state with a lectin was studied.

  DOI：

  10.1021/ja411522f