(1,2-dideoxy-α-D-galactofuranoso)[1,2-d]-1,3-oxazolidine-2-thione | 2654-55-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1,2-dideoxy-α-D-galactofuranoso)[1,2-d]-1,3-oxazolidine-2-thione
• 英文别名: N,O²-thiocarbonyl-α-D-galactofuranosylamine；(3aS,5S,6S,6aR)-5-[(1R)-1,2-dihydroxyethyl]-6-hydroxy-3a,5,6,6a-tetrahydro-3H-furo[2,3-d][1,3]oxazole-2-thione
• CAS: 2654-55-9
• 化学式: C₇H₁₁NO₅S
• 分子量: 221.234
• InChiKey: PKBVCSNCOXHULL-PHYPRBDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (1,2-dideoxy-α-D-galactofuranoso)[1,2-d]-1,3-oxazolidine-2-thione 在 吡啶 作用下， 反应 24.0h， 以84%的产率得到N-acetyl-(3,5,6-tri--O-acetyl-1,2-dideoxy-α-D-galactofuranoso)[1,2-d]-1,3-oxazolidine-2-thione
  参考文献：
  名称：

  Synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl-β-d-galactofuranosyl isothiocyanate

  摘要：

  Per-O-tert-butyldimethylsilyl-alpha,beta-D-galactofuranosyl isothiocyanate (4) was synthesized by the reaction of per-O-TBS-beta-D-galactofuranose (1) with KSCN, promoted by TMSI. Upon O-desilylation (1,2-dideoxy-alpha-D-galactofuranoso)[1,2d]-1,3-oxazolidine-2-thione (6), the cis-fused bicyclic thiocarbamate was obtained as the only product. Conformational analysis, aided by molecular modelling, showed two stable twist forms (T-3(4) and T-4(o)) for the five-membered sugar ring in 6. In aqueous solution, the equilibrium favours the first conformation (3:1 ratio). On the other hand, this ratio decreases for less polar solvents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.013
• 作为产物：
  描述：

  2,3,5,6-tetra-O-tert-butyldimethylsilyl-α-D-galactofuranosyl isothiocyanate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以76%的产率得到(1,2-dideoxy-α-D-galactofuranoso)[1,2-d]-1,3-oxazolidine-2-thione
  参考文献：
  名称：

  Synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl-β-d-galactofuranosyl isothiocyanate

  摘要：

  Per-O-tert-butyldimethylsilyl-alpha,beta-D-galactofuranosyl isothiocyanate (4) was synthesized by the reaction of per-O-TBS-beta-D-galactofuranose (1) with KSCN, promoted by TMSI. Upon O-desilylation (1,2-dideoxy-alpha-D-galactofuranoso)[1,2d]-1,3-oxazolidine-2-thione (6), the cis-fused bicyclic thiocarbamate was obtained as the only product. Conformational analysis, aided by molecular modelling, showed two stable twist forms (T-3(4) and T-4(o)) for the five-membered sugar ring in 6. In aqueous solution, the equilibrium favours the first conformation (3:1 ratio). On the other hand, this ratio decreases for less polar solvents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.013