期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 39, 页码 13544-13548出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201502521
关键词
1,1 '-alpha-glycosylation; total synthesis; Mycobacterium gordonae; regioselective glycosylation; trehalose oligosaccharides
资金
- Department of Science and Technology [SR/S1/OC-40/2009]
- Board of Research in Nuclear Sciences [2013/37C/51/BRNS]
- IRCC
- IITB [09IRCC001]
- CSIR-New Delhi
- RIFC, IRCC
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.
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