1-O-benzyl-2-N,3-O-thiocarbonyl-β-D-fructofuranosylamine | 575472-02-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-benzyl-2-N,3-O-thiocarbonyl-β-D-fructofuranosylamine
• 英文别名: (3aR,5R,6R,6aS)-6-hydroxy-5-(hydroxymethyl)-3a-(phenylmethoxymethyl)-3,5,6,6a-tetrahydrofuro[2,3-d][1,3]oxazole-2-thione
• CAS: 575472-02-5
• 化学式: C₁₄H₁₇NO₅S
• 分子量: 311.359
• InChiKey: VVKNEJWTTJWMIU-NRWUCQMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-benzyl-2-N,3-O-thiocarbonyl-β-D-fructofuranosylamine 在 咪唑 、 碳酸氢钠 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 1-O-benzyl-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 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-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

• Conformationally Restricted Oxazolidin‐2‐one Fused Bicyclic Iminosugars as Potential Glycosidase Inhibitors
  作者：Maria Domingues、Justyna Jaszczyk、Maria Isabel Ismael、José Albertino Figueiredo、Richard Daniellou、Pierre Lafite、Marie Schuler、Arnaud Tatibouët

  DOI：10.1002/ejoc.202001053

  日期：2020.10.15

  The synthesis of unprecedented bicyclic oxazolidin‐2‐one (OZO) fused iminosugars is described. The key step involves a tandem Staudinger/retro Michael/aza Michael sequence from OZO azidosugars, themselves obtained through oxidation of oxazolidin‐2‐thione (OZT) precursors. The iminosugars were subsequently evaluated as glycosidase inhibitors.

  描述了前所未有的双环恶唑烷-2-酮（OZO）融合亚氨基糖的合成。关键步骤涉及来自OZO叠氮糖的串联Staudinger /复古Michael /氮杂Michael序列，它们本身是通过恶唑烷-2-硫酮（OZT）前体的氧化获得的。随后将亚氨基糖评估为糖​​苷酶抑制剂。
• Small libraries of fused quinazolinone-sugars. Access to quinazolinedione nucleosides
  作者：Jolanta Girniene、Guillaume Apremont、Arnaud Tatibouët、Algirdas Sackus、Patrick Rollin

  DOI：10.1016/j.tet.2004.01.032

  日期：2004.3

  Unprotected carbohydrates can readily be converted into base-modified nucleosides and deoxynucleosides through a short sequence involving the condensation of anthranilic acid derivatives with a suitably protected sugar-derived 2-alkylthio-1,3-oxazoline. (C) 2004 Elsevier Ltd. All rights reserved.
• Base-modified nucleosides from carbohydrate derived oxazolidinethiones: a five-step process
  作者：Jolanta Girniene、David Gueyrard、Arnaud Tatibouët、Algirdas Sackus、Patrick Rollin

  DOI：10.1016/s0040-4039(01)00357-4

  日期：2001.4

  Starting from unprotected carbohydrates, base-modified nucleosides could be reached in four steps through the condensation of anthranilic acid with a suitably protected sugar-derived 2-alkylthio-1,3-oxazoline. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.