Fmoc-L-Cys(β-D-Glc)-OH | 1533407-92-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-L-Cys(β-D-Glc)-OH
• CAS: 1533407-92-9
• 化学式: C₂₄H₂₇NO₉S
• 分子量: 505.546
• InChiKey: RZICREDSCQCSIE-CTAFWJRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.51
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  165.78
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Fmoc-L-Cys(β-D-Glc)-OH 、 乙酸酐 在 磷酸 作用下， 以 水 为溶剂， 反应 2.0h， 以47%的产率得到N^α-fluoren-9-ylmethoxycarbonyl-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-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
• 作为产物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 S-β-D-glucopyranosyl-L-cysteine hydrochloride 在 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 以59%的产率得到Fmoc-L-Cys(β-D-Glc)-OH
  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