97614-41-0

Usage

Uses

Used in Pharmaceutical Industry:
1,3,5-Tri-O-benzoyl-2-O-(trifluoromethanesulfonyl)-a-D-ribofuranose is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with improved properties, such as enhanced stability, solubility, and bioavailability.
Used in Positron-Emission Tomography (PET) Probes:
1,3,5-Tri-O-benzoyl-2-O-(trifluoromethanesulfonyl)-a-D-ribofuranose is used as a building block in the production of PET probes. PET is a medical imaging technique that uses radioactive tracers to visualize the metabolic processes within the body. 1,3,5-Tri-O-benzoyl-2-O-(trifluoromethanesulfonyl)-a-D-ribofuranose plays a crucial role in the development of new PET probes, which can help in the early detection and diagnosis of various diseases, including cancer and neurological disorders.

InChI:InChI=1/C27H21F3O10S/c28-27(29,30)41(34,35)40-22-21(38-24(32)18-12-6-2-7-13-18)20(16-36-23(31)17-10-4-1-5-11-17)37-26(22)39-25(33)19-14-8-3-9-15-19/h1-15,20-22,26H,16H2

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 

Downstream Products

• 97614-43-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose 
• 314289-50-4 (2R,3S,4R,5R)-5-((benzoyloxy)methyl)-3-[¹⁸F]fluoro-tetrahydrofuran-2,4-diyl dibenzoate 
• 98855-71-1 ((2R,3R,4S)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate 
• 1093278-47-7 (2R,3S,4R,5R)-5-((benzoyloxy)methyl)-3-chlorotetrahydrofuran-2,4-diyl dibenzoate 
• 55734-52-6 Di-O-benzoyl-2-brom-2-deoxy-D-arabinosylbromid 
• 93688-61-0 C₁₀H₁₀ClN₅O₃ 
• 1093278-48-8 C₁₉H₁₆BrClO₅ 
• 1093278-65-9 2-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-chloro-β-D-arabinofuranosyl)-adenine 
• 1052670-08-2 1-bromo-2-⁽¹⁸⁾F-fluoro-3,5-di-O-benzoyl-D-arabinofuranose 
• 1052670-13-9 C₂₃H₂₀⁽¹⁸⁾FN₃O₆ 

Relevant academic research and scientific papers

SITE-SPECIFIC ANTIBODY-DRUG CONJUGATES BY ADP-RIBOSYL CYCLASES

Antibody-drug conjugates, compositions thereof, and methods use. The antibody-drug conjugates include a fusion protein comprising an antibody covalently linked to an ADP-ribosyl cyclase protein via a peptide linker moiety at one or more of a C-terminus or N-terminus of a heavy or light chain of the antibody, a NAD or NMN analogue, and a payload such that the NAD or NMN analogue is conjugated to both the payload and the ADP-ribosyl cyclase protein.

Stereoinversion of Stereocongested Carbocyclic Alcohols via Triflylation and Subsequent Treatment with Aqueous N,N-Dimethylformamide

A convenient method for the stereoinversion of secondary alcohols, applicable to stereocongested carbocyclic substrates, is reported. A simple three-step procedure, including triflylation of the hydroxy group, nucleophilic oxygenative displacement by the treatment with aqueous N,N-dimethylformamide (DMF), and methanolysis, allowed for efficient stereoinversion of various substrates, including sugar derivatives, in one pot.

Isolation, synthesis, and characterization of impurities and degradants from the clofarabine process

The identification of clofarabine process impurities and their subsequent isolation, synthesis, and characterization is described. Two isomeric process impurities resulting from N6-attachment of a fluoroarabinose to clofarabine were found. Clofarabine's base degradation products, which were different from the process impurities, were also synthesized and characterized. These compounds resulted from modifications to the sugar moiety, the purine ring, or both. A mechanistic rationale for the formation of the various process impurities and degradation products is provided.

Direct and convenient conversion of alcohols to fluorides

Directly mixing primary, secondary, and tertiary alcohols with nC 4F9SO2F-NR3(HF)3-NR 3 in THF or MeCN results in convenient conversion to the corresponding fluorides in high yields. The readily available reagents are easy to handle, and the mild, almost neutral reaction conditions allow for excellent functional group compatibility. A NR3(HF)3/NR3 ratio of ≤ 1:2 gives the highest reactivity.

Synthesis and NMR conformational studies of stable analogues of 2-deoxy-α-D-ribose-1-phosphate

Malonate ethers and phosphonate derivatives of 2-deoxyribose and 2-deoxy-2-fluoroarabinose have been synthesized, for the first time, as stable analogues of 2-deoxy-α-D-ribose-1-phosphate (1). In almost all the cases, the α-anomers have been obtained as the major isomers. The NMR conformational analysis performed indicate a similar conformational equilibria for the natural phosphate 1 and the here described analogues, with the exception of the glycosyl phosphonate 3α. None of the compounds were inhibitory to purified E. coli thymidine phosphorylase at 250 μM. Also, when administered to intact CEM cells, no inhibitory effect was observed in hypoxanthine and inosine metabolising enzymes, including purine nucleoside phosphorylase.