142706-48-7

Upstream product

• 96253-10-0 1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione 
• 1666-13-3 diphenyl diselenide 
• 135824-30-5 1-<3-deoxy-3-(phenylseleno)-5-O-trityl-β-D-arabinofuranosyl>uracil 
• 56889-16-8 3'-O-mesyl-2',5'-di-O-trityluridine 
• 134100-02-0 3'-O-mesyl-2',5'-di-O-pivaloyluridine 
• 134100-03-1 1-(3-deoxy-3-phenylseleno-2,5-di-O-pivaloyl-β-D-xylofuranosyl)uracil 

Downstream Products

• 132364-17-1 1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl]uracil 
• 135824-37-2 1-<2-O-acetyl-5-O-(tert-butyldimethylsilyl)-3-deoxy-3-(phenylseleno)-β-D-arabinofuranosyl>uracil 
• 135928-55-1 1-[(2R,3R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-4-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 134100-05-3 Propionic acid (2R,3S,4S,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-phenylselanyl-tetrahydro-furan-3-yl ester 
• 134100-19-9 Acetic acid (2R,3S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-[1-phenyl-meth-(E)-ylidene]-tetrahydro-furan-3-yl ester 
• 134100-14-4 Acetic acid (2R,3S,4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(hydroxy-phenyl-methyl)-tetrahydro-furan-3-yl ester 
• 134100-04-2 Acetic acid (2R,3S,4S,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-phenylselanyl-tetrahydro-furan-3-yl ester 
• 134100-08-6 1-[(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(hydroxy-phenyl-methyl)-3-oxo-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Allylic substitution of 3′,4′-unsaturated nucleosides: Organosilicon-based stereoselective access to 4′-C-branched 2′,3′-didehydro-2′,3′-dideoxyribonucleosides

Reactions of organosilicon reagents (such as allyltrimethylsilane, silyl enol ethers, cyanotrimethylsilane) with 3′,4′-unsaturated nucleosides (of uracil, N4-acetylcytosine, and hypoxanthine) having an allyl ester structure were investigated in

Uracil and Adenine Nucleosides Having a 2',3'-Bromovinyl Structure: Highly Versatile Synthons for the Synthesis of 2'-C- and 3'-C-Branched 2',3'-Unsaturated Derivatives

Preparation of 2'- and 3'-bromo derivatives of 2',3'-unsaturated uracil and adenine nucleosides has been carried out starting from the corresponding β-hydroxyselenides by way of bromination and successive selenoxide elimination.These compounds have been shown to serve as versatile synthons for the preparation of anti-HIV candidates, 2'-C- and 3'-C-branched 2',3'-unsaturated nucleosides, through palladium-catalyzed cross-coupling and halogen-lithium exchange reactions. Key Words: β-hydroxyselenide; bromovinyl structure; branched-sugar nucleoside; anti-HIV agent; 2',3'-unsaturated nucleoside.

Selenoxide Elimination for the Synthesis of Unsaturated-Sugar Uracil Nucleosides

Introduction of a phenylseleno group to the sugar portion of uracil nucleosides and selenoxide elimination reactions of the resulting selenium-containing derivatives are described.A phenylselenide anion prepared by reducing (PhSe)2 with LiAlH4 was found to be highly reactive.By using this selenide as a nucleophile, ring openings of various types of cyclonucleosides and nucleosides having an anhydro structure in the sugar portion were accomplished.The products, which contain a phenylseleno group in the sugar portion, were oxidized with m-CPBA in CH2Cl2, and their susceptibility to the selenoxide elimination and regiochemistry of the reaction was investigated.

Nucleosidic enol esters: A versatile tool for the synthesis of 3'-carbon-substituted nucleosides

Enol esters of uracil and adenine nucleosides prepared by selenoxide fragmentation of the corresponding 3'-phenylseleno derivatives have been shown to yield 3'-carbon-substituted products upon reacting with MeLi followed by electrophiles, providing the fi