1243310-70-4Relevant articles and documents
The methylsulfonylethoxymethyl (Msem) as a hydroxyl protecting group in oligosaccharide synthesis
Ali, Asghar,Van Den Berg, Richard J.B.H.N.,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Codée, Jeroen D.C.
experimental part, p. 6121 - 6132 (2010/10/21)
The methylsulfonylethoxymethyl (Msem) is introduced as a base-labile, non-participating protecting group in carbohydrate chemistry. Conditions to introduce the Msem on primary and secondary alcohols are described. Removal of the Msem is best achieved using a catalytic amount of tetrabutylammonium fluoride (TBAF), with or without a nucleophilic scavenger. Applicability of the Msem group is illustrated in the assembly of an all 1,3-cis-linked mannotrioside.