1,4,6-tri-O-tert-butyldimethylsilyl-2-N,3-O-thiocarbonyl-β-D-fructofuranosylamine | 117922-42-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4,6-tri-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-3a,5-bis[[tert-butyl(dimethyl)silyl]oxymethyl]-3,5,6,6a-tetrahydrofuro[2,3-d][1,3]oxazole-2-thione
• CAS: 117922-42-6
• 化学式: C₂₅H₅₃NO₅SSi₃
• 分子量: 564.022
• InChiKey: IRFUMVVHCFAXJI-MVOHMCPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.79
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 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：

  1,4,6-tri-O-tert-butyldimethylsilyl-2-N,3-O-thiocarbonyl-β-D-fructofuranosylamine 在 镍 作用下， 生成 5-Amino-1-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-2,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-tetrahydro-furan-2-yl]-1H-imidazole-4-carboxylic acid amide
  参考文献：
  名称：

  A novel stereospecific synthesis of 5-amino-1-β-D-fructofuranosylimidazole-4-carboxamide

  摘要：

  一种β-D-果糖呋喃糖融合的噻唑烷-2-硫酮已作为t-丁基二甲基硅基衍生物（6）被分离出来，该衍生物在脱硫后与α-氨基-α-氰基乙酰胺反应，生成了硅化的1-β-D-果糖呋喃糖氨基咪唑（2b），该化合物在用甲醇盐酸脱去保护基后，产生了5-氨基-β-D-果糖呋喃糖-咪唑-4-羧酰胺（2a）。

  DOI：

  10.1039/c39880000671
• 作为产物：
  描述：

  D-fructose 、 potassium thioacyanate 、 叔丁基二甲基氯硅烷 在 盐酸 、 咪唑 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 以20%的产率得到1,4,6-tri-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

• GROUILLER, ANNIE;MACKENZIE, GRAHAME;NAJIB, BOUBKER;SHAW, GORDON;EWING, DA+, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 10, 671-672
  作者：GROUILLER, ANNIE、MACKENZIE, GRAHAME、NAJIB, BOUBKER、SHAW, GORDON、EWING, DA+

  DOI：——

  日期：——
• A novel stereospecific synthesis of 5-amino-1-β-<scp>D</scp>-fructofuranosylimidazole-4-carboxamide
  作者：Annie Grouiller、Grahame Mackenzie、Boubker Najib、Gordon Shaw、David Ewing

  DOI：10.1039/c39880000671

  日期：——

  A β-D-fructofuranose fused oxazolidine-2-thione has been isolated as the t-butyldimethylsilyl derivative (6), which when desulphurised and treated with α-amino-α-cyanoacetamide gave the silylated 1-β-D-fructofuranosyl aminoimidazole (2b) which when deblocked with methanolic hydrogen chloride produced 5-amino-β-D-fructofuranosyl-imidazole-4-carboxamide (2a).

  一种β-D-果糖呋喃糖融合的噻唑烷-2-硫酮已作为t-丁基二甲基硅基衍生物（6）被分离出来，该衍生物在脱硫后与α-氨基-α-氰基乙酰胺反应，生成了硅化的1-β-D-果糖呋喃糖氨基咪唑（2b），该化合物在用甲醇盐酸脱去保护基后，产生了5-氨基-β-D-果糖呋喃糖-咪唑-4-羧酰胺（2a）。
• 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.