117162-37-5Relevant academic research and scientific papers
Hydrophilically augmented glycosyl carborane derivatives for incorporation in antibody conjugation reagents
Maurer, Julie L.,Serino, Anthony J.,Hawthorne, M. Frederick
, p. 2519 - 2524 (1988)
The synthesis of a series of O-glycosyl carboranes is described. The reactions of hydroxyalkyl carboranes and esterified carbohydrates, in the presence of a Lewis acid catalyst, proved to be stereoselective. Reactions of these carboranes with tri-O-acetyl-D-glucal or di-O-acetyl-D-xylal and a catalytic amount of BF3·OEt2 favored the formation of α anomers, while the β anomer was the major product of the SnCl4-catalyzed reaction involving hydroxymethyl carborane and 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose. The 1H and 13C NMR spectra of 1-[(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)methyl]-1, 2-dicarba-closo-dodecaborane (3) were analyzed by using several one-dimensional and two-dimensional techniques; the chemical shifts and coupling interactions of all atoms were unequivocally assigned.
