An armed-disarmed approach for blocking aglycon transfer of thioglycosides

Tetrahedron Lett. 2007 Jan 22;48(4):559-562. doi: 10.1016/j.tetlet.2006.11.126.

Abstract

Thioglycosides are used frequently as glycosyl donors and as mimetics of O-glycosides. While being very useful, thioglycosides are prone to a detrimental side reaction referred to as aglycon transfer. In this paper, it is shown that aglycon transfer can be blocked by matching thioglycoside-containing acceptors with more armed glycosyl donors.