848397-74-0Relevant articles and documents
Total Synthesis of Trisaccharide Repeating Unit of O-Specific Polysaccharide of Pseudomonas fluorescens BIM B-582
Behera, Archanamayee,Rai, Diksha,Kushwaha, Divya,Kulkarni, Suvarn S.
supporting information, p. 5956 - 5959 (2018/09/21)
The first total synthesis of the trisaccharide repeating unit of the O-specific polysaccharide of Pseudomonas fluorescens BIM B-582 is reported. This efficient synthesis involves consecutive 1,2-cis glycosylations including β-l-rhamnosylation and α select
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.
Disarming, non-participating 2-O-protecting groups in manno- and rhamnopyranosylation: Scope and limitations of sulfonates, vinylogous esters, phosphates, cyanates, and nitrates
Crich, David,Hutton, Thomas K.,Banerjee, Abhisek,Jayalath, Prasanna,Picione, John
, p. 105 - 119 (2007/10/03)
A series of d-mannopyranosyl and l-rhamnopyranosyl thioglycosides protected with electron-withdrawing, non-participating protecting groups on O-2 have been prepared and investigated for their potential as β-glycosyl donors. Both α- and β-thioglycosides we
