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Expedient Synthesis of a Linear Nonadecaarabinofuranoside of the Mycobacterium tuberculosis Cellular Envelope
Author(s) -
Mishra Bijoyananda,
Manmode Sujit,
Panda Ravi Raja Adhikari,
Hotha Srinivas
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700712
Subject(s) - chemistry , glycosylation , mycobacterium tuberculosis , glycosyl , total synthesis , yield (engineering) , stereochemistry , chemical synthesis , combinatorial chemistry , oligosaccharide , biochemistry , tuberculosis , in vitro , medicine , materials science , pathology , metallurgy
The synthesis of oligosaccharides is demanding as it requires multiple steps and long reaction sequences. The choice of glycosylation method and protecting groups is very important for the successful synthesis of any oligosaccharide. In this paper, we show that ethynylcyclohexyl carbonate glycosyl donors are excellent for the synthesis of a nonadecasaccharide fragment of the Mycobacterium tuberculosis glycocalyx using a split/react/couple strategy. The synthesis of the target nonadecasaccharide was accomplished using eight different reactions and 23 steps in 6.4 % overall yield.