85372-91-4

Usage

InChI:InChI=1/C16H16N2O7/c19-7-10-12(21)13(22)15(25-10)18-6-9(14(23)17-16(18)24)11(20)8-4-2-1-3-5-8/h1-6,10,12-13,15,19,21-22H,7H2,(H,17,23,24)/t10-,12-,13-,15-/m1/s1

Upstream product

• 110522-95-7 5-Benzoyl-1-[(2R,3R,4R,5R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 64898-15-3 2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine 
• 98-88-4 benzoyl chloride 
• 100-52-7 benzaldehyde 
• 362-43-6 2',3'-O-isopropylideneuridine 
• 92471-83-5 5-benzoyl-2',3'-O-isopropylidene-5'-O-methoxymethyl-5,6-dihydrouridine 
• 85372-74-3 2',3'-O-isopropylidene-5'-O-methoxymethyl-5,6-dihydrouridine 
• 80614-78-4 2',3'-O-isopropylidene-5'-O-methoxymethyl-uridine 
• 85372-86-7 5-benzoyl-2',3'-O-isopropylidene-5'-O-methoxymethyluridine 

Relevant academic research and scientific papers

A SIMPLE AND GENERAL ENTRY TO 5-SUBSTITUTED URUDINES BASED ON THE REGIOSELECTIVE LITHIATHION CONTROLLED BY A PROTECTING GROUP IN THE SUGAR MOIETY

Lithiathion of 2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine with sec-BuLi/TMEDA occurs at the C-5 position with a high regioselectivity and subsequent reactions of the resulting C-5 lithiated species with a variety of electrophiles provides a general entry to 5-substituted uridines.

LITHIATION OF 5,6-DIHYDROURIDINE: A NEW ROUTE TO 5-SUBSTITUTED URIDINES

2',3'-O-Isopropylidene-5'-O-methoxymethyl-5,6-dihydrouridine (2) was found to serve as an "amide α-anion" upon lithiation with LDA.Reactions of the anion with acid chlorides followed by phenylselenation and oxidative elimination furnished 5-acyluridines.For the preparation of 5-alkyluridines, initial introduction of phenylselenenyl group at the C-5 of 2 appeared to be effective.Alkylation of its α-selenenyl carbanion and subsequent generation of 5,6-double bond produced 5-alkyluridines.These routes constitute a new entry to 5-substituted uridines.