76832-97-8

Upstream product

• 76832-95-6 Methyl 3,5-Di-O-benzyl-2-O-(trifluoromethanesulfonyl)-α-D-ribofuranoside 
• 55775-39-8 1-O-methyl-3,5-di-O-benzyl-D-ribofuranoside 
• 329360-22-7 1-O-methyl-3,5-di-O-benzyl-α-D-arabinofuranose 
• 4860-82-6 2,3-anhydro-α-D-ribofuranoside de methyle 
• 20187-72-8 methyl 2,3-anhydro-5-O-benzyl-α-D-ribofuranoside 

Relevant academic research and scientific papers

Fluoroglycolactone synthesis method

The invention discloses a synthesis method of fluoro sugar lactone. According to the method, D-xylose is taken as a starting raw material, hydroxyl is protected to synthesize a lactonide compound intermediate, and then the fluoroglycolactone is obtained through the steps of stereo conversion of sugar cyclic alcohol, benzyl addition, methyl glycoside removal, hydroxyl oxidation and the like. The raw materials adopted by the synthesis method are simple, cheap and easy to obtain, each synthesis step is mild in condition, the treatment process is simple, the yield is relatively high, and new raw materials and synthesis ways are provided for design of fluorine-containing bioactive molecules.

Furanosyl Oxocarbenium Ion Conformational Energy Landscape Maps as a Tool to Study the Glycosylation Stereoselectivity of 2-Azidofuranoses, 2-Fluorofuranoses and Methyl Furanosyl Uronates

The 3D shape of glycosyl oxocarbenium ions determines their stability and reactivity and the stereochemical course of SN1 reactions taking place on these reactive intermediates is dictated by the conformation of these species. The nature and co

New fluorinated fructose analogs as selective probes of the hexose transporter protein GLUT5

Facilitated hexose transporters (GLUTs) mediate the transport of hexoses and other substrates across the membranes of numerous cell types, and while some are expressed ubiquitously (e.g., GLUT1), others are more tissue specific (e.g., GLUT5). These properties have been exploited for the imaging of cancer cells by the use of hexose based probes, including fluorinated hexose derivatives for use with positron emission tomography (PET). However, design of new probes has been hampered by a limited understanding of how GLUT transporters interact with their substrates at the molecular level. Two fluorinated fructose surrogates designed for uptake by the GLUT5 transporter are described here: 3-deoxy-3-fluoro-d-fructose (3-FDF) and 1-deoxy-1-fluoro-2,5-anhydromannitol (1-FDAM). Synthesis (both cold and radiolabeled) and in vitro analysis of their transport characteristics in two breast cancer cell lines (EMT-6 and MCF-7) expressing GLUT5 are detailed. Both analogues are readily taken up into both cancer cell lines, with uptake mediated primarily by GLUT5. They also have low IC50 values, indicating a high affinity for the transporter, suggesting that the uptake of these probes would be unaffected by endogenously circulating fructose. Selective uptake by GLUT5 was also demonstrated in Xenopus oocytes. Finally, these results are the first demonstration that a hexose existing predominantly in the pyranose ring structure (3-FDF) is transported by GLUT5, strongly suggesting that this transporter can handle both furanose and pyranose forms of fructose.

Facile Synthesis of 2-Deoxy-2-substituted-D-arabinofuranose Derivatives

Several methyl 2-deoxy-2-substituted-D-arabinofuranosides (4a-e and 5b-e) to be used as intermediates in the synthesis of 2'-substituted arabinonucleosides of biomedical interest were prepared by treatment of methyl 3,5-di-O-benzyl-2-O-(trifluoromethanesu