Recent advances in stereoselective glycosylation through intramolecular aglycon delivery.
Methodology toward the stereoselective 1,2-cis glycoside linkage using intramolecular aglycon delivery (IAD) has been extensively developed. In the last two decades, progress has been made using various mixed acetal linkages and a number of glycosyl donor moieties to develop novel IAD strategies, mainly based on formation of acetal linkages. This account summarizes the newest naphthylmethyl (NAP) ether-mediated IAD as well as all the types of mediations for stereospecific construction of various 1,2-cis linkages, not only for beta-mannopyranoside, but also for other linkages almost without exception, including beta-L-rhamnoside.
Ishiwata
Akihiro
A
RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. aishiwa@riken.jp
Lee
Yong Joo
YJ
Ito
Yukishige
Y
D000080:Acetals / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000080:Acetals; D006027:Glycosides; D007659:Ketones