91345-19-6

Basic information

• Product Name: 2′-O-benzoyl-L-threonolactone
• Synonyms: 2′-O-benzoyl-L-threonolactone
• CAS NO: 91345-19-6
• Molecular Weight: 222.197
• Mol File: 91345-19-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2′-O-benzoyl-L-threonolactone(CAS DataBase Reference)
• NIST Chemistry Reference: 2′-O-benzoyl-L-threonolactone(91345-19-6)
• EPA Substance Registry System: 2′-O-benzoyl-L-threonolactone(91345-19-6)

Safety Data

• Hazardous Substances Data: 91345-19-6(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 70753-61-6 calcium L-threonate 
• 21730-93-8 L-threonic acid-4-lactone 

Downstream Products

• 1446785-28-9 2-O-Benzoyl-3-O-tert-butyldiphenylsilyl-L-threonolactone 
• 1446785-49-4 N⁶-benzoyl-9-(2′-O-benzoyl-3′-O-tert-butyldiphenylsilyl-α-L-threofuranosyl)adenine 
• 325684-00-2 1-(2′-O-benzoyl-α-L-threofuranosyl)thymine 
• 1446785-56-3 N⁶-benzoyl-9-(2′-O-benzoyl-α-L-threofuranosyl)adenine 
• 537690-82-7 1-{2'-O-benzoyl-3'-O-[(4,4'-dimethoxytriphenyl)methyl]-α-L-threofuranosyl}thymine 
• 849778-77-4 1'α-(N⁶-benzoyladenin-9-yl)-2'-O-benzoyl-3'-O-diisopropyl-phosphonomethyl-L-threose 

Relevant articles and documents

A Scalable Synthesis of α-L-Threose Nucleic Acid Monomers

Recent advances in polymerase engineering have made it possible to copy information back and forth between DNA and artificial genetic polymers composed of TNA (α-l-threofuranosyl-(3′,2′) nucleic acid). This property, coupled with enhanced nuclease stability relative to natural DNA and RNA, warrants further investigation into the structural and functional properties of TNA as an artificial genetic polymer for synthetic biology. Here, we report a highly optimized chemical synthesis protocol for constructing multigram quantities of TNA nucleosides that can be readily converted to nucleoside 2′-phosphoramidites or 3′-triphosphates for solid-phase and polymerase-mediated synthesis, respectively. The synthetic protocol involves 10 chemical transformations with three crystallization steps and a single chromatographic purification, which results in an overall yield of 16-23% depending on the identity of the nucleoside (A, C, G, T).

NOVEL ANTIVIRAL COMPOUNDS, A PROCESS FOR THEIR PREPARATION, AND THEIR USE FOR TREATING VIRAL INFECTIONS

The present invention relates to novel pro-drugs of L-2'-deoxythreose nucleoside phosphonates, such as phosphoramidate, phosphorodiamidate and phospho-diester prodrugs. The invention also relates to a process for preparing these novel prodrugs of nucleoside phosphonates. The invention also relates to the use of these novel phosphonatemodified nucleosides to treat or prevent viral infections and their use to manufacture a medicine to treat or prevent viral infections, particularly infections with viruses belonging to the HBV family.

Synthesis of α- L -threose nucleoside phosphonates via regioselective sugar protection

A new synthesis route to α-l-threose nucleoside phosphonates via 2-O and 3-O selectively protected l-threose is developed. The key intermediates 2-O-benzoyl-l-threonolactone and 1-O-acetyl-2-O-benzoyl-3-O-t- butyldiphenylsilyl-l-threofuranose were functionalized to synthesize 2′-deoxy-2′-fluoro- and 3′-C-ethynyl l-threose 3′-O-phosphonate nucleosides. The key intermediates developed are important intermediates for the synthesis of new l-threose-based nucleoside analogues, TNA phosphoramidites, and TNA triphosphates.