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First Total Synthesis of Trehalose-Containing Branched Oligosaccharide OSE-1 of Mycobacterium gordonae (Strain 990)

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Title First Total Synthesis of Trehalose-Containing Branched Oligosaccharide OSE-1 of Mycobacterium gordonae (Strain 990)
 
Creator CHAUBE, MA
KULKARNI, SS
 
Subject GLYCOSYL DONORS
CONVERGENT SYNTHESIS
REPEATING UNIT
N-GLYCAN
TUBERCULOSIS
BENZYLIDENE
ANALOGS
SUGARS
LIPOPOLYSACCHARIDE
1,1-DISACCHARIDES
1,1 '-alpha-glycosylation
total synthesis
Mycobacterium gordonae
regioselective glycosylation
trehalose oligosaccharides
 
Description The first total synthesis of the branched oligosaccharide OSE-1 of Mycobacterium gordonae (strain 990) is reported. An intramolecular aglycon delivery approach was used for constructing the desymmetrized 1,1-,-linked trehalose moiety. A [3+2] glycosylation of the trisaccharide donor and trehalose acceptor furnished the right hand side pentasaccharide. Regioselective O3 glycosylation of L-rhamnosyl 2,3-diol allowed expedient synthesis of the left hand side tetrasaccharide. The nonasaccharide was assembled in a highly convergent fashion through a [4+5] glycosylation.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2016-01-14T10:32:42Z
2016-01-14T10:32:42Z
2015
 
Type Article
 
Identifier CHEMISTRY-A EUROPEAN JOURNAL, 21(39)13544-13548
0947-6539
1521-3765
http://dx.doi.org/10.1002/chem.201502521
http://dspace.library.iitb.ac.in/jspui/handle/100/17368
 
Language en