5458-82-2

Basic information

• Product Name: 3,5-di-O-acetyl-1,2-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-allofuranose
• Synonyms: 3,5-di-O-acetyl-1,2-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-allofuranose
• CAS NO: 5458-82-2
• Molecular Weight: 458.486
• Mol File: 5458-82-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3,5-di-O-acetyl-1,2-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-allofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-di-O-acetyl-1,2-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-allofuranose(5458-82-2)
• EPA Substance Registry System: 3,5-di-O-acetyl-1,2-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-allofuranose(5458-82-2)

Safety Data

• Hazardous Substances Data: 5458-82-2(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 26275-20-7 6-deoxy-1,2-O-isopropylidene-6-(4'-methylbenzene)sulfonyloxy-D-glucofuranose 
• 2595-05-3 Diacetone D-glucose 
• 363148-72-5 3-O-acetyl-1,2-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-allofuranose 
• 51433-05-7 3'-O-acetyl-1',2'-O-isopropylidene-5',6'-diol-α-D-allofuranose 
• 29474-72-4 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 
• 98-59-9 p-toluenesulfonyl chloride 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 2280-44-6 D-Glucose 

Downstream Products

• 98693-59-5 Acetic acid (S)-1-((R)-1-acetoxy-ethyl)-4-[(2,4-dinitro-phenyl)-hydrazono]-butyl ester 
• 120968-82-3 (1R)-O²-acetyl-O³,O⁵-dibenzoyl-1-(6-benzoylamino-purin-9-yl)-1,4-anhydro-6-deoxy-D-glucitol 
• 122331-59-3 1,2-Di-O-acetyl-3,5-di-O-benzoyl-6-desoxy-D-glucofuranose 
• 51785-66-1 3,5-Di-O-benzoyl-6-desoxy-1,2-O-isopropyliden-α-D-glucofuranose 
• 17668-66-5 6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 

Relevant articles and documents

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.