133180-99-1

Upstream product

• 67-56-1 methanol 
• 79-37-8 oxalyl dichloride 
• 29412-62-2 cubane-1,4-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

CUBANE NUCLEOSIDE ANALOGS

Cubane nucleoside analogs useful as anti-viral and anti-cancer agents are provided herein. Methods for preparing cubane nucleoside analogs are also provided. The invention also provides pharmaceutical compositions containing one or more cubane nucleoside analogs and one or more pharmaceutically acceptable carriers, excipients, or diluents. The invention also provides methods for treating cancer and viral infections in mammals. The cubane nucleosides describe herein are compound of the general formula (I) in which B is an optionally substituted purine or pyrimidines nucleoside base and R1, R2, R3, R4, R5, R6, and R7 are defined herein.

Photochemical Functionalization of Cubanes

A wide range of cubanecarboxylic acids has been prepared by a simple and efficient photochemical process.Chlorocarbonylation of cubanecarboxylic acid with oxalyl chloride under UV irradiation produced polysubstituted cubanes with chlorocarbonyl groups predominantly on the remote sites (β or γ).The Td-tetraacid chloride 6b, in which chlorocarbonyl groups are in alternate positions, was the major product.Irradiation of 1,2,3,7-tetrasubstituted cubane 9 with oxalyl chloride gave pentasubstituted cubane 10.Other isomers, 1,3,5,7-tetrasubstituted cubane 6 and 1,2,4,7-tetrasubstituted cubane 8, in which chlorocarbonylation would occur at positions ortho to three or two carbonyl groups, gave only chlorinated products.Photochemical reaction of oxalyl chloride with nitrocubanes gave chlorocarbonylated and chlorinated nitrocubanes.Ab initio calculations show carbon-hydrogen bond strength at different positions of the cubane is not the major factor in determining the regioselectivity of the chlorocarbonylation.A polar effect might be the key factor in site selectivity.