186839-91-8

Upstream product

• 58-96-8 uridine 
• 3587-60-8 Benzyloxymethyl chloride 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 186839-90-7 3-[(benzyloxy)methyl]-1-(β-D-ribofuranosyl)uracil 

Downstream Products

• 1134031-92-7 C₃₀H₅₀N₂O₇Si₂ 
• 1134031-80-3 C₃₀H₅₀N₂O₇Si₂ 
• 186839-95-2 Bromo-acetic acid (2R,4S,5R)-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-tetrahydro-furan-2-ylmethyl ester 
• 186839-97-4 3-Benzyloxymethyl-1-[(2R,3R,3aR,7aR)-3-(tert-butyl-dimethyl-silanyloxy)-3a-hydroxy-5-oxo-hexahydro-furo[2,3-c]pyran-2-yl]-1H-pyrimidine-2,4-dione 
• 186839-93-0 3-Benzyloxymethyl-1-[(2R,3S,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-4-oxo-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 186839-92-9 3-Benzyloxymethyl-1-[(2R,3S,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-oxo-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Synthetic studies towards the identification of novel capuramycin analogs with mycobactericidal activity

Expeditious syntheses of capuramycin, an effective MraY inhibitor in vivo, analogs are described. Synthetic schemes reported here are extremely useful for the generation of capuramycin analogs to identify minimum structure requirement to exhibit antimycobactericidal activity.

Nucleosides and Nucleotides. 163. Synthesis of 3′-β-Branched Uridine Derivatives via Intramolecular Reformatsky-Type Reaction Promoted by Samarium Diiodide

A novel efficient method for the synthesis of 3′-β-branched uridines starting from uridine was developed, in which a SmI2-promoted intramolecular Reformatsky-type reaction was effectively used. 5′-O-(Bromoacetyl)-3′-ketouridine derivatives 12, 26, and 27 were synthesized from uridine and were subjected to an intramolecular Reformatsky-type reaction. When 12, 26, and 27 were treated with 2.0 equiv of SmI2 in THF at -78°C, intramolecular carbon-carbon bond formation at the 3′-β-position proceeded smoothly to give the corresponding 3′,5′-lactones 14, 28, and 29 in high yields, respectively. Treatment of 28 with NH3/MeOH gave the 3′-β-branched uridine derivative 32 quantitatively, which was then deprotected to give 3′-C-(carbamoylmethyl)uridine (33).