1-O-benzyl-4,6-di-O-tert-butyldimethylsilyl-2-N,3-O-thiocarbonyl-β-D-fructofuranosylamine | 575472-06-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-benzyl-4,6-di-O-tert-butyldimethylsilyl-2-N,3-O-thiocarbonyl-β-D-fructofuranosylamine
• 英文别名: (3aR,5R,6R,6aS)-6-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3a-(phenylmethoxymethyl)-3,5,6,6a-tetrahydrofuro[2,3-d][1,3]oxazole-2-thione
• CAS: 575472-06-9
• 化学式: C₂₆H₄₅NO₅SSi₂
• 分子量: 539.884
• InChiKey: PLYUTVSAVMSQOY-ZUVQJFRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  90.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-benzyl-4,6-di-O-tert-butyldimethylsilyl-2-N,3-O-thiocarbonyl-β-D-fructofuranosylamine 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 1-O-benzyl-2-N-tert-butoxycarbonyl-4,6-di-O-tert-butyldimethylsilyl-2-N,3-O-carbonyl-β-D-fructofuranosylamine
  参考文献：
  名称：

  Inhibition of the d-fructose transporter protein GLUT5 by fused-ring glyco-1,3-oxazolidin-2-thiones and -oxazolidin-2-ones

  摘要：

  The glucose transporter 5 (GLUT5)-a specific D-fructose transporter-belongs to a family of facilitating sugar transporters recently enlarged by the human genome sequencing. Prompted by the need to develop specific photolabels of these isoforms, we have studied the interaction of conformationally locked D-fructose and L-sorbose derived 1,3-oxazolidin-2-thiones and 1,3-oxazolidin-2-ones to provide a rational basis for an interaction model. The inhibition properties of the D-fructose transporter GLUT5 by glyco-1,3-oxazolidin-2-thiones and glyco-1,3-oxazolidin-2-ones is now reported. In vitro, the fused-rings systems tested showed an efficient inhibition of GLUT5, thus bringing new insights on the interaction of D-fructose with GLUT5. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00007-7
• 作为产物：
  描述：

  果糖二丙酮 在 咪唑 、 sodium hydride 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 1-O-benzyl-4,6-di-O-tert-butyldimethylsilyl-2-N,3-O-thiocarbonyl-β-D-fructofuranosylamine
  参考文献：
  名称：

  Inhibition of the d-fructose transporter protein GLUT5 by fused-ring glyco-1,3-oxazolidin-2-thiones and -oxazolidin-2-ones

  摘要：

  The glucose transporter 5 (GLUT5)-a specific D-fructose transporter-belongs to a family of facilitating sugar transporters recently enlarged by the human genome sequencing. Prompted by the need to develop specific photolabels of these isoforms, we have studied the interaction of conformationally locked D-fructose and L-sorbose derived 1,3-oxazolidin-2-thiones and 1,3-oxazolidin-2-ones to provide a rational basis for an interaction model. The inhibition properties of the D-fructose transporter GLUT5 by glyco-1,3-oxazolidin-2-thiones and glyco-1,3-oxazolidin-2-ones is now reported. In vitro, the fused-rings systems tested showed an efficient inhibition of GLUT5, thus bringing new insights on the interaction of D-fructose with GLUT5. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00007-7

文献信息

• Regioselective N-vinylation of cyclic thionocarbamates through a vinyl bis-sulfone methodology
  作者：Jolanta Girniene、Sébastien Tardy、Arnaud Tatibouët、Algirdas Sačkus、Patrick Rollin

  DOI：10.1016/j.tetlet.2004.06.124

  日期：2004.8

  A vinyl bis-sulfone Michael type approach towards heteroatom vinylation was applied on nitrogen derivatives. Cyclic thionocarbamates-mainly 1,3-oxazolidine-2-thiones-were converted into their N-vinyl counterparts; the procedure proved particularly efficient in the case of carbohydrate-derived complex structures. (C) 2004 Published by Elsevier Ltd.
• Inhibition of the d-fructose transporter protein GLUT5 by fused-ring glyco-1,3-oxazolidin-2-thiones and -oxazolidin-2-ones
  作者：Jolanta Girniene、Arnaud Tatibouët、Algirdas Sackus、Jing Yang、Geoffrey D Holman、Patrick Rollin

  DOI：10.1016/s0008-6215(03)00007-7

  日期：2003.4

  The glucose transporter 5 (GLUT5)-a specific D-fructose transporter-belongs to a family of facilitating sugar transporters recently enlarged by the human genome sequencing. Prompted by the need to develop specific photolabels of these isoforms, we have studied the interaction of conformationally locked D-fructose and L-sorbose derived 1,3-oxazolidin-2-thiones and 1,3-oxazolidin-2-ones to provide a rational basis for an interaction model. The inhibition properties of the D-fructose transporter GLUT5 by glyco-1,3-oxazolidin-2-thiones and glyco-1,3-oxazolidin-2-ones is now reported. In vitro, the fused-rings systems tested showed an efficient inhibition of GLUT5, thus bringing new insights on the interaction of D-fructose with GLUT5. (C) 2003 Elsevier Science Ltd. All rights reserved.