38359-55-6

Usage

Usage

Plasticizer in industrial and consumer products

Function

Increases flexibility and resilience of plastics

Additional Uses

Solvent in chemical processes, binder in paint and coating formulations

Durability

Makes plastics more resistant to wear and tear

Health Risks

Potential toxicity and environmental impact

Current Status

Under investigation for safety

Ongoing Efforts

Development of safer alternatives in industrial processes

InChI:InChI=1/C16H14N2O6/c19-12-8-11(9-23-15(21)10-4-2-1-3-5-10)24-14(12)18-7-6-13(20)17-16(18)22/h1-7,11,14H,8-9H2,(H,17,20,22)/t11-,14+/m0/s1

Upstream product

• 98-88-4 benzoyl chloride 
• 54898-43-0 1-(5-hydroxymethyl-3-oxo-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 
• 38431-65-1 1-(5-O-benzoyl-2,3-O-dimesyl-β-D-lyxo-furanosyl) uracil 
• 38359-53-4 1-(5-O-benzoyl-3-O-mesyl-2-tosyl-β-D-lyxo-furanosyl)uracil 
• 4348-61-2 uridine 
• 161016-65-5 1-(2,3-dideoxy-2-N-morpholino-5-O-trityl-β-D-glycero-pent-2-enofuranosyl) uracil 
• 95906-48-2 1-(5'-O-triphenylmethyl-3'-deoxy-β-D-glycero-pentofuran-2-ulosyl)uracil 
• 146763-12-4 2',3'-di-O-mesyl-5'-O-trityl-(1-β-D-lyxofuranosyl)uracil 

Downstream Products

• 5983-05-1 1-(5-O-benzoyl-3-deoxy-β-D-ara-furanosyl)uracil 
• 126187-05-1 5'-O-benzoyl-2',3'-dideoxy-2'-oxo-α-uridine 

Relevant academic research and scientific papers

5'-O-benzoyl-2'-keto-3'-deoxy-α-uridine: First unambiguous synthesis, crystal structure and its use to establish the anomerisation of 2'-ketouridines under basic conditions

5'-O-benzoyl-3'-deoxy-2'-keto-α-uridine was characterised unambiguously with the help of crystal structure analysis and provided 1H-NMR data to differentiate it from its β-anomer. We have also established, with the help of the above 1H-NMR data that the earlier reported procedures of synthesising 2'-ketouridine produced a mixture of anomers.

Reactions of 2′,3′-Di-O-mesyl-lyxo-uridine with secondary amines: First report on the one-pot conversion of mesylated nucleosides to enaminonucleosides and the crystal structure of α-enamine

2′,3′-Di-O-mesyl-5′-O-trityl-lyxo-uridine 1 reacted with secondary amines to produce enaminonucleosides 2a-d and 3a-d. Intermediacy of 2′-ketouridine was essential for the anomerisation and enamine formation to take place. The structure of the β-enamine was established unambiguously by analysing the hydrolysed product and that of α-enamine was proved with the help of crystal structure analysis.

Synthesis of 1-(3′-deoxy-β-D-glycero-pentofuran-2′-ulosyl)uracil by selective elimination reactions

For the synthesis of y 1-(3′-deoxy-β-D-glycero-pentofuran-2′-ulosyl)uracil (16), the precursor, 5′-O-benzoyl derivative (2),2 was elaborated in a variety of ways. 1-(5′-O-Benzoyl-3′-O-tosyl-β-D- lyxofuranosyl)uracil (4)2 was benzoylated to N3-benzoyl-1-(2′,5′-di-O-benzoyl-3′-O-tosyl-β-D- lyxofuranosyl)uracil (5), which directly yielded 2 on treatment with sodium benzoate. 1-(3′,5′-Di-O- benzoyl-2′-O-tosyl-β-D-lyxofuranosyl)uracil (8) and its 3′,5′-O-isopropylidene analog (10) resisted elimination reactions, thus proving absolute selectivity in the elimination of the derivatives of 1-β-D- lyxofuranosyl-uracil. Seeking a more economical path to 2, 1-(5′-O-benzoyl-β-D-lyxofuranosyl)uracil (11) was first benzoylated to give 2′,5′-di-O-benzoate (12), accompanied by 3′,5′-di- and 2′,3′,5′-tri-O- benzoate. Mesylation of the major product (12) gave 1-(2′,5′-di-O-benzoyl-3′-O-mesyl-β-D- lyxofuranosyl)uracil (15), which, on treatment with sodium benzoate, gave 2 in an highly improved yield. Basic hydrolysis on 2 gave compound 16.