359017-30-4

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 37699-02-8 2,5-anhydro-3,4,6-tri-O-benzyl-aldehydo-D-altrohexofuranose 

Downstream Products

• 421553-97-1 ethyl 3-amino-3-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)propenoate 
• 474081-72-6 (4R)-6-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-4-(3-hydroxyphenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester 
• 474081-83-9 (4R)-6-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-4-[2-(trifluoromethyl)phenyl]-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester 
• 474081-84-0 (4S)-6-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-4-[2-(trifluoromethyl)phenyl]-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester 
• 474081-85-1 (4R)-4-(2',3',4',6'-tetra-O-benzyl-β-D-mannopyranosyl)-6-(2'',3'',5''-tri-O-benzyl-β-D-ribofuranosyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester 
• 359408-29-0 6-((2S,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-4-phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester 
• 501101-30-0 diethyl (4R)-2-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-1,4-dihydro-6-methyl-4-[2-(trifluoromethyl)phenyl]pyridine-3,5-dicarboxylate 

Relevant academic research and scientific papers

Towards the synthesis of C-glycosylated dihydropyrimidine libraries via the three-component Biginelli reaction. A novel approach to artificial nucleosides

The Lewis acid catalyzed (BF3·Et2O, CuCl, AcOH) one-pot three-component cyclocondensation of urea with C-glycosylated aldehydes and β-keto esters (Biginelli reaction) in a combinatorial manner afforded three different series of 3,4-dihydropyrimidin-2(1H)-ones bearing C-glycosyl moieties at C4, C6, and at both C4 and C6.

Three-component biginelli cyclocondensation reaction using C-glycosylated substrates. Preparation of a collection of dihydropyrimidinone glycoconjugates and the synthesis of C-glycosylated monastrol analogues

The aldehyde-ketoester-urea cyclocondensation reaction has been revisited using C-glycosylated reagents with the aim of exploring a potential entry to a library of dihydropyrimidinone glycoconjugates. A collection of 13 mono- and bis-C-glycosylated dihydropyrimidinones has been prepared by a parallel synthesis approach using the three-component promoter CuCl/AcOH/BF3· Et2O. The sugar residues have been installed at either N1, C4, or C6 in the monoglycosylated derivatives and at both the C4 and C6 in the bisglycosylated products. The mono- and bisglycosylated products at C4 and C6 were obtained as mixtures of diastereoisomers with good to excellent selectivities due to the asymmetric induction by the sugar residue in the formation of the C4 stereocenter of the dihydropyrimidinone ring. Individual stereoisomers were isolated as pure compounds and their structures assigned with the aid of X-ray crystallography and chiroptical properties. As a demonstration of this new concept in the Biginelli reaction, the synthesis of two C4 epimer monastrol analogues bearing the ribofuranosyl moiety at C6 has been described.