5-thio-D-fructofuranose

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: 5-thio-D-fructofuranose
• 英文别名: D-5-thio-fructose；5-Thio-d-fructo-furanose；(3S,4S,5R)-2,5-bis(hydroxymethyl)thiolane-2,3,4-triol
• 化学式: C₆H₁₂O₅S
• 分子量: 196.224
• InChiKey: BGTAQEJBEWTQED-VRPWFDPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  126
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 5-thio-D-fructofuranose 在 zinc(II) chloride 作用下， 生成 1,3,4,6-Tetra-O-acetyl-5-S-acetyl-5-thioketo-D-fructose
  参考文献：
  名称：

  5-Thio-D-fructofuranose

  摘要：

  DOI：

  10.1021/jo00893a021
• 作为产物：
  描述：

  3-O-benzoyl-1,2-O-isopropylidene-β-D-fructopyranose 在 吡啶 、 咪唑 、 三氟化硼乙醚 、 碘 、 sodium methylate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 126.0h， 生成 5-thio-D-fructofuranose
  参考文献：
  名称：

  d-Fructose–l-sorbose interconversions. Access to 5-thio-d-fructose and interaction with the d-fructose transporter, GLUT5

  摘要：

  Epimerisation and subsequent functionalization at C-5 of D-fructopyranose derivatives under Mitsunobu and Garegg's conditions provided efficient access to 5-thio-D-fructose (2) as well as to 5-azido-5-deoxy-1,2-O-isopropylidene-beta -D-fructopyranose (19), a known precursor to 2,5-deoxy-2,5-imino-D-mannitol (3). The interaction of 2 with the D-fructose transporter GLUTS, was found to be weaker than that of D-fructose, a result that suggests involvement of the ring oxygen atom in the recognition of D-fructose by GLUTS. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00153-7

文献信息

• d-Fructose–l-sorbose interconversions. Access to 5-thio-d-fructose and interaction with the d-fructose transporter, GLUT5
  作者：Arnaud Tatibouët、Myriam Lefoix、Jonathan Nadolny、Olivier R Martin、Patrick Rollin、Jing Yang、Geoffrey D Holman

  DOI：10.1016/s0008-6215(01)00153-7

  日期：2001.7

  Epimerisation and subsequent functionalization at C-5 of D-fructopyranose derivatives under Mitsunobu and Garegg's conditions provided efficient access to 5-thio-D-fructose (2) as well as to 5-azido-5-deoxy-1,2-O-isopropylidene-beta -D-fructopyranose (19), a known precursor to 2,5-deoxy-2,5-imino-D-mannitol (3). The interaction of 2 with the D-fructose transporter GLUTS, was found to be weaker than that of D-fructose, a result that suggests involvement of the ring oxygen atom in the recognition of D-fructose by GLUTS. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 5-Thio-D-fructofuranose
  作者：Marek Chmielewski、Roy L. Whistler

  DOI：10.1021/jo00893a021

  日期：1975.3