297747-20-7Relevant academic research and scientific papers
Reciprocal donor acceptor selectivity (RDAS): A new concept for matching donors with acceptors
Fraser-Reid, Bert,Lopez, J. Cristobal,Radhakrishnan,Mach, Mateusz,Schlueter, Urs,Gomez, Ana,Uriel, Clara
, p. 1075 - 1087 (2007/10/03)
Lemieux's extensive work on replacement reactions at the anomeric center helped to establish the fact that the O-2-protecting group of a donor exerts powerful control over stereoselectivity in glycoside coupling reactions. This manuscript shows that the O-2-protecting group of a donor also exerts powerful, indeed sometimes total, control over regioselectivity in glycosidation of diols. The latter acceptors also exhibit preferences over the donor, thereby providing evidence for the concept of reciprocal donor acceptor selectivity (RDAS). The latter concept is put to the test by simultaneously presenting an acceptor diol with equivalent amounts of two donors, in the hope of achieving double differential glycosidation leading to one-pot assembly of a trisaccharide. When the pair of donors did not conform to RDAS principles the reaction did not proceed beyond a dissacharide. However, when the pair was RDAS sanctioned, a single trisaccharide (out of four possibilities) was obtained.
Targeted glycosyl donor delivery for site-selective glycosylation.
Anilkumar,Nair,Fraser-Reid
, p. 2587 - 2589 (2007/10/03)
[reaction: see text]n-Pentenyl ortho esters (NPOEs) and n-pentenyl glycosides (NPGs) are interconvertible glycosyl donors which are activated by reaction with halonium ions. In a series of cyclic syn-1,3-diols, NPOEs have been found to specifically glycos
