108257-55-2Relevant articles and documents
The development of N-aryl trifluoroacetimidate-based benzyl and allyl protecting group reagents
Tsabedze, Sinele B.,Kabotso, Daniel E.K.,Pohl, Nicola L.B.
supporting information, p. 6983 - 6985 (2013/12/04)
An exploration of the role of para-substituents on the balance between stability and reactivity of N-phenyl trifluoroacetimidates prompted the discovery of new reagents for the addition of allyl and benzyl protecting groups, namely O-allyl and O-benzyl N-
Rapid preparation of variously protected glycals using titanium(III)
Spencer, Roxanne P.,Cavallaro, Cullen L.,Schwartz, Jeffrey
, p. 3987 - 3995 (2007/10/03)
Glycosyl chlorides and bromides can be rapidly converted to glycals in high yield by reaction with (Cp2Ti[III]Cl)2. This reagent tolerates a wide range of common carbohydrate protecting groups, including silyl ethers, acetals, and esters; the methodology provides a general route for the preparation of glycals substituted with both acid- and base-labile functionality. A reaction mechanism is proposed that is based on heteroatom abstraction to give an intermediate glycosyl radical. This radical reacts with a second equivalent of Ti(III) to yield a glycosyltitanium(IV) species. β-Heteroatom elimination from the glycosyltitanium(IV) complex gives the glycal.
