363148-72-5

Upstream product

• 51433-05-7 3'-O-acetyl-1',2'-O-isopropylidene-5',6'-diol-α-D-allofuranose 
• 98-59-9 p-toluenesulfonyl chloride 
• 2595-05-3 Diacetone D-glucose 
• 29474-72-4 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 

Downstream Products

• 5458-82-2 3,5-di-O-acetyl-1,2-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-allofuranose 

Relevant academic research and scientific papers

Synthesis and preclinical characterization of 1-(6′-deoxy-6′-[18F]fluoro-β-D-allofuranosyl)-2-nitroimidazole (β-6′-[18F]FAZAL) as a positron emission tomography radiotracer to assess tumor hypoxia

Positron emission tomography (PET) using fluorine-18 (18F)-labeled 2-nitroimidazole radiotracers has proven useful for assessment of tumor oxygenation. However, the passive diffusion-driven cellular uptake of currently available radiotracers results in slow kinetics and low tumor-to-background ratios. With the aim to develop a compound that is actively transported into cells, 1-(6′-deoxy-6′-[18F]fluoro-β-D-allofuranosyl)-2-nitroimidazole (β-[18F]1), a putative nucleoside transporter substrate, was synthetized by nucleophilic [18F]fluoride substitution of an acetyl protected labeling precursor with a tosylate leaving group (β-6) in a final radiochemical yield of 12?±?8% (n?=?10, based on [18F]fluoride starting activity) in a total synthesis time of 60?min with a specific activity at end of synthesis of 218?±?58?GBq/μmol (n?=?10). Both radiolabeling precursor β-6 and unlabeled reference compound β-1 were prepared in multistep syntheses starting from 1,2:5,6-di-O-isopropylidene-α-D-allofuranose. In vitro experiments demonstrated an interaction of β-1 with SLC29A1 and SLC28A1/2/3 nucleoside transporter as well as hypoxia specific retention of β-[18F]1 in tumor cell lines. In biodistribution studies in healthy mice β-[18F]1 showed homogenous tissue distribution and excellent metabolic stability, which was unaffected by tissue oxygenation. PET studies in tumor bearing mice showed tumor-to-muscle ratios of 2.13?±?0.22 (n?=?4) at 2?h after administration of β-[18F]1. In ex vivo autoradiography experiments β-[18F]1 distribution closely matched staining with the hypoxia marker pimonidazole. In conclusion, β-[18F]1 shows potential as PET hypoxia radiotracer which merits further investigation.

Chiral diphosphites derived from D-glucose: New ligands for the asymmetric catalytic hydroformylation of vinyl arenes

A series of novel diphosphite ligands derived from readily available D-(+)-glucose has been synthesized. These ligands have been applied to the Rh-catalyzed hydroformylation of vinyl arenes. Both excellent enantioselectivities (up to 91%) and regioselectivities (up to 98.8%) were achieved under mild conditions. The advantage of these ligands is that their modular natures allow facile, systematic variation in the configurations at the stereocenters [C(3), C(5)] at the ligand bridge and in the biphenyl substituents, enabling their effects on the stereoselectivity to be studied. Results show that the absolute configuration of the product is governed by the configuration at the stereogenic center C(3), while the level of the enantioselectivity is influenced by a cooperative effect between stereocenters C(3) and C(5). Replacement of the tert-butyl substituent by methoxy substituents at the para positions of the biphenyl moieties improved the enantioselectivities. We have characterized the rhodium complexes formed under CO/H2 by NMR techniques and in situ IR spectroscopy and have observed that there is a relationship between the structure of the [HRh(CO)2(PP)] species and their enantiodiscriminating performance in hydroformylation. Enantio-selectivities were highest with ligands with a strong bis-equatorial coordination preference, while an equilibrium of species with bis-equatorial and equatorial-axial coordination modes considerably reduced the ee's.