Cbz-D-Cys(α-D-GlcNAc)-OBn | 1533407-91-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Cbz-D-Cys(α-D-GlcNAc)-OBn
• CAS: 1533407-91-8
• 化学式: C₂₆H₃₂N₂O₉S
• 分子量: 548.614
• InChiKey: WEIQKOOJHSIZHH-VSHXEECHSA-N

物化性质

• 沸点：
  846.4±65.0 °C(predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  163.65
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Cbz-D-Cys(α-D-GlcNAc)-OBn 、 乙酸酐 在 吡啶 作用下， 反应 1.0h， 以57%的产率得到S-((tri-O-acetyl)-2-acetamido-2-deoxy-α-D-glucosyl)-N-Cbz-D-cysteine benzyl ester
  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-glucosyl)-D-cysteine hydrochloride 在 碳酸氢钠 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 Cbz-D-Cys(α-D-GlcNAc)-OBn
  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