93612-81-8Relevant articles and documents
New protected protecting groups for the 5′-hydroxy group of deoxynucleosides by use of 2-(hydroxymethyl)- and 2-[(methylamino)methyl]benzoyl skeletons and oxidatively cleavable tritylthio and (4-methoxytrityl)thio groups
Seio, Kohji,Utagawa, Eri,Sekine, Mitsuo
, p. 2318 - 2333 (2004)
The new protecting groups 1a,b and 2a,b were developed for the 5′-OH group of deoxynucleosides by utilizing the unique characters of the sulfenate and sulfenamide linkage. These new protecting groups have a 2-(hydroxymethyl) benzoyl or 2-[(methylamino)met
2-(Prenyloxymethyl)benzoyl (POMB) as a new temporary protecting group for alcohols
Vatèle, Jean-Michel
, p. 2299 - 2301 (2007/10/03)
The 2-(prenyloxymethyl)benzoyl (POMB) group was introduced in high yields to hydroxyl functions using the crystalline reagent, 2-(prenyloxymethyl)benzoic acid, in the presence of dicyclohexylcarbodiimide (DCC) and 4- dimethylaminopyridine (DMAP). 2-(Prenyloxymethyl)benzoic acid is readily available, in two steps, from phthalide in 65% overall yield. The POMB group can be cleaved, in two steps, by treatment with 2,3-dichloro-5,6-dicyanoquinone (DDQ) followed by intramolecular lactonisation of the resulting hydroxy ester induced by a catalytic amount of Yb(OTf)3·H2O. The reaction conditions are compatible with the presence of a number of protecting groups such as isopropylidene, benzyl, acetyl, chloroacetyl, benzoyl, levulinoyl, Fmoc and Boc groups.