methyl (2R)-2-((4R,5S)-4,5-dimethyl-4-hydroxy-5-methoxy-2-oxooxazolidin-3-yl)-3-(tetra-O-acetyl-β-D-glucosylthio)propanoate | 1533407-80-5

• 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: methyl (2R)-2-((4R,5S)-4,5-dimethyl-4-hydroxy-5-methoxy-2-oxooxazolidin-3-yl)-3-(tetra-O-acetyl-β-D-glucosylthio)propanoate
• CAS: 1533407-80-5
• 化学式: C₂₄H₃₅NO₁₅S
• 分子量: 609.606
• InChiKey: PSXOXKMPTZCIBK-BUDJJISTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.13
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  199.73
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  methyl (2R)-2-((4R,5S)-4,5-dimethyl-4-hydroxy-5-methoxy-2-oxooxazolidin-3-yl)-3-(tetra-O-acetyl-β-D-glucosylthio)propanoate 在 盐酸 作用下， 以 水 为溶剂， 以94%的产率得到S-β-D-glucopyranosyl-L-cysteine hydrochloride
  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：

  1-硫代-b-D-葡萄糖四乙酸酯 、 methyl 2-((4R,5S)-4,5-dimethyl-4-hydroxy-5-methoxy-2-oxooxazolidin-3-yl)acrylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以79%的产率得到methyl (2R)-2-((4R,5S)-4,5-dimethyl-4-hydroxy-5-methoxy-2-oxooxazolidin-3-yl)-3-(tetra-O-acetyl-β-D-glucosylthio)propanoate
  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