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First Total Synthesis of Trehalose‐Containing Branched Oligosaccharide OSE‐1 of Mycobacterium gordonae (Strain 990)
Author(s) -
Chaube Manishkumar A.,
Kulkarni Suvarn S.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502521
Subject(s) - glycosylation , moiety , trisaccharide , tetrasaccharide , chemistry , trehalose , oligosaccharide , stereochemistry , strain (injury) , intramolecular force , biochemistry , biology , polysaccharide , anatomy
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′‐α,α‐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.